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inquiryAdvantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
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inquiryHenan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod
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inquiryEstablished in May 2015, TaiChem Ltd. is initially invested by a British research and development company and started by PhDs back from aboard. The company is registered in China Medical City (CMC), Taizhou, Jiangsu Province, and the production site
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inquiryAnsciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali
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inquiryHangzhou Utanpharma Biology Co., Ltd. is a R&D and manufacturing based, market oriented enterprise,specialized in the R&D and marketing of active pharmaceutical ingredients and intermediates. Supported by our highly qualified professor and
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inquiry(2S,4S)-N-(tert-butyloxycarbonyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In tert-Amyl alcohol at 0℃; for 5.25h; Cooling with ice; | 70% |
Stage #1: (2S,4S)-N-(tert-butyloxycarbonyl)pyrrolidine-2,4-dicarboxylic acid dimethyl ester With water; sodium hydroxide In tetrahydrofuran at 0℃; for 5h; Stage #2: With hydrogenchloride In water | 70% |
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 5.25h; | 70% |
(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C 1.2: 12 h / 20 °C 2.1: water; sodium hydroxide / tert-Amyl alcohol / 5.25 h / 0 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane; methanol / 16 h / 20 °C 1.3: 12 h / 20 °C 2.1: sodium hydroxide; water / tetrahydrofuran / 5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 16 h / 20 °C 1.2: 12 h / 20 °C 2.1: sodium hydroxide; water / tetrahydrofuran / 5 h / 0 °C View Scheme |
di-tert-butyl dicarbonate
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; ethyl acetate / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 5.25 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: ethyl acetate / 0.1 h / Industrial scale 2.1: water; sodium hydroxide / tetrahydrofuran / -1 °C / Industrial scale 2.2: pH 1 / Industrial scale View Scheme | |
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 16 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 5 h / 0 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; ethyl acetate / 12 h / 20 °C 2: sodium hydroxide / tetrahydrofuran; water / 5.25 h / 0 °C View Scheme |
(2S,4S)-pyrrolidine-2,4-dicarboxylic acid dimethyl ester
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 16 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 5 h / 0 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-N-(tert-butyloxycarbonyl)-4-(hydroxymethyl)-pyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.75h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 2h; | 60% |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 2: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
chloroformic acid ethyl ester
(2S,4S)-N-(tert-butyloxycarbonyl)-4-(hydroxymethyl)-pyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid; chloroformic acid ethyl ester With triethylamine In tetrahydrofuran at 0℃; for 0.75h; Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 2h; | 60% |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,5S)-2-(2-(9-((2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 5-methylpyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / acetone / 16 h / 40 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,4S)-2-(5-{2-[(2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidin-2-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / acetone / 16 h / 40 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 24 h / 110 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / acetone / 16 h / 40 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 24 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 505 h / 40 °C 8: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1.5 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S,3S)-1-[(2S,5S)-2-(5-{2-[(2S,4S)-1-{(2S,3S)-2-[(methoxycarbonyl)amino]-3-methylpentanoyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-5-methylpyrrolidin-l-yl]-3-methyl-1-oxopentan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / acetone / 16 h / 40 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 24 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 505 h / 40 °C 8: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 1.5 h 9: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,4S)-2-(5-{2-[(2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidin-2-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-5-methylpyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / acetone / 16 h / 40 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 24 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 505 h / 40 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-2-(2-(9-((2S,4S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-methylpyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 16 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 16 h / 50 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,5S)-2-(9-{2-[(2S,5S)-1-(tert-butoxycarbonyl)-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,4,5,11-tetrahydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 16 h / 50 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 20 h / 110 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,4S)-2-[5-(2-{(2S,4S)-1-[N-(methoxycarbonyl)-L-valyl]-4-(methoxymethyl)pyrrolidin-2-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-methylpyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 16 h / 50 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 20 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 15 h / 35 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 16 h / 50 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 20 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 15 h / 35 °C 8: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 5 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S,3R)-3-methoxy-1-[(2S,4S)-2-[9-(2-{(2S,4S)-1-[N-(methoxycarbonyl)-O-methyl-L-threonyl]-4-methylpyrrolidin-2-yl}-1H-imidazol-5-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-1-oxobutan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 16 h / 50 °C 6: ammonium acetate / toluene; 2-methoxy-ethanol / 20 h / 110 °C 7: manganese(IV) oxide / dichloromethane / 15 h / 35 °C 8: hydrogenchloride / dichloromethane; 1,4-dioxane; methanol / 5 h 9: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.58 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-1-tert-butyl 2-(2-oxo-2-(8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)ethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-2-(2-(9-bromo-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 1-tert-butyl 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: borane-THF / 2-methyltetrahydrofuran; tetrahydrofuran / 25 °C / Industrial scale 2.1: water; sodium hydroxide / tert-butyl methyl ether / 2 h / 0.1 - 0.2 °C / Industrial scale 2.2: 0.2 h / 0.5 °C / Industrial scale 3.1: sodium t-butanolate / tetrahydrofuran / 0 h / 0.1 - 0.2 °C / Industrial scale 4.1: potassium carbonate / dichloromethane / 0.2 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2R,4R)-1-tert-butyl 2-(2-(9-((2S,5S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-5-methylpyrrolidine-2-carbonyloxy)-8-oxo-8,9,10,11-tetrahydro-5H-dibenzo[c,g]chromen-3-yl)-2-oxoethyl) 4-(methoxymethyl)pyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,4,5,11-tetrahydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[N-(methoxycarbonyl)-L-valyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h View Scheme | |
Multi-step reaction with 8 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h View Scheme | |
Multi-step reaction with 9 steps 1.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 4.1: borane dimethyl sulfide complex / tetrahydrofuran / 22 h / 0 - 20 °C 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide; sodium hydrogencarbonate; sodium hypochlorite / dichloromethane; water / 2 h / 20 °C 6.1: ammonium hydroxide / water; methanol / 20 °C 7.1: iodine; sodium carbonate / 1,4-dioxane / Darkness 8.1: sodium thiosulfate / ethanol; water / 22 h / 90 - 100 °C 9.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; dimethyl sulfoxide / 5 h / 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 9 steps 1.1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / dichloromethane / 3 h / 0 - 20 °C 3.1: methanol; lithium hydroxide / tetrahydrofuran / 2 h / 20 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 22 h / 0 - 20 °C 5.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite; sodium bromide / dichloromethane / 2 h / 20 °C 6.1: ammonium hydroxide / water; methanol / 20 °C 7.1: iodine; sodium carbonate / 1,4-dioxane / Darkness 8.1: sodium dithionite / ethanol; water / 22 h / 90 - 100 °C 9.1: tetrakis(triphenylphosphine) palladium(0); (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; dimethyl sulfoxide / 5 h / 95 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S,3S)-1-[(2S,4S)-2-(5-{2-[(2S,5S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-5-methylpyrrolidin-2-yl]-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 11: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.1 h View Scheme | |
Multi-step reaction with 9 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h 9.1: hydrogenchloride / dichloromethane / 1 h / 20 °C 9.2: 0.1 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(1R)-2-[(2S,4S)-2-(5-{2-[(2S,5S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-5-methylpyrrolidin-2-yl]-1,4,5,11-tetrahydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl}-1H-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 0.5 h / 20 °C 10: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 0.33 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-1-tert-butyl 2-methyl 4-((difluoromethoxy)methyl)pyrrolidine-1,2-dicarboxylate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: copper(l) iodide / acetonitrile / 1 h / 45 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: copper(l) iodide / acetonitrile / 1 h / 45 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-1-(tert-butoxycarbonyl)-4-((difluoromethoxy)methyl)pyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: copper(l) iodide / acetonitrile / 1 h / 45 °C 4: water; lithium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: copper(l) iodide / acetonitrile / 1 h / 45 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 1 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2R)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 11: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h 9.1: hydrogenchloride / ethanol / 3 h / 50 °C 9.2: 2 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: hydrogenchloride / dichloromethane; 1,4-dioxane / 0.5 h / 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 11: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 3 h View Scheme | |
Multi-step reaction with 9 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h 9.1: hydrogenchloride / ethanol / 3 h / 50 °C 9.2: 3 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
methyl {(2S)-1-[(2S,5S)-2-(9-{2-[(2S,4S)-1-{(2S,3S)-3-methoxy-2-[(methoxycarbonyl)amino]butanoyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1H-imidazol-5-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C 5: caesium carbonate / 4 h / 20 °C 6: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 7: caesium carbonate / 20 h / 50 °C 8: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 9: manganese(IV) oxide / dichloromethane / 13 h 10: hydrogenchloride / dichloromethane; 1,4-dioxane / 1 h / 20 °C 11: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 3 h View Scheme | |
Multi-step reaction with 9 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: caesium carbonate / 2-methyltetrahydrofuran / 4 h / 20 °C 5.1: pyridinium hydrobromide perbromide / dichloromethane; methanol / 1.75 h / 20 °C 6.1: caesium carbonate / 2-methyltetrahydrofuran / 20 h / 50 °C 7.1: ammonium acetate / toluene; 2-methoxy-ethanol / 4.5 h / 110 °C 8.1: manganese(IV) oxide / dichloromethane / 13 h 9.1: hydrogenchloride / ethanol / 3 h / 50 °C 9.2: 3 h View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-N-(tert-butyloxycarbonyl)-4-(methoxymethyl)-pyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice View Scheme | |
Multi-step reaction with 2 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 2: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 °C 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C View Scheme |
(3S,5S)-N-(tert-butoxycarbonyl)-5-(methoxycarbonyl)-pyrrolidine-3-carboxylic acid
(2S,4S)-N-(tert-butyloxycarbonyl)-4-(methoxymethyl)-pyrrolidine-2-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C / Cooling with ice 2: water; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 °C / Cooling with ice 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice 4: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.75 h / 0 °C 1.2: 2 h / 0 °C 2.1: 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate / 3 h / 0 - 20 °C 3.1: water; lithium hydroxide / methanol; tetrahydrofuran / 2 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 2: sodium tetrahydroborate / tetrahydrofuran; water / 2 h / 0 °C 3: silver trifluoromethanesulfonate; 2,6-di-tert-butyl-pyridine / dichloromethane / 3 h / 0 - 20 °C 4: lithium hydroxide / tetrahydrofuran; methanol; water / 2 h / 20 °C View Scheme |
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