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inquiryHebei yanxi chemical co., LTD is a professional research, development and production 2-phenylacetamide enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carbon environ
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inquiryBoc-3-Hydroxy-1-adamantyl-D-glycine CAS No.:361442-00-4 Name: Boc-3-Hydroxy-1-adamantyl-D-glycine Synonyms (alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.1(3,7)]decane-1-acetic acid Molecul
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inquiryCangzhou Enke Pharma Tech Co.,ltd. is located in Cangzhou City, Hebei province ,where is a famous petroleum chemical industry city in China. Enke Pharma a high-tech enterprise ,and we are dedicated to developing and manufacturing new api, intermedi
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inquiryAbout Product Details
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inquiryLIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc.
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inquiry(alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid Basic information Product Name: (alphaS)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-hy
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inquiryProduct Name: Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No.: 361442-00-4 Molecular formula: C17H27NO5 Molecular weight: 325 Appearance: white powder Storage:Store in cool and dry place, away from
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inquiryProduct Description Product Name Boc-3-Hydroxy-1-adamantyl-D-glycine CAS No. 361442-00-4 Appearance White powder
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inquiry(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide In ethanol at 18 - 65℃; for 2h; | 98.1% |
di-tert-butyl dicarbonate
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 20℃; for 12h; | 98% |
With potassium phosphate In tetrahydrofuran; sodium hydroxide at 20℃; for 2h; | 88% |
Stage #1: (αS)-α-amino-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; di-tert-butyl dicarbonate With sodium hydroxide for 4h; pH=10; Stage #2: With sulfuric acid In Isopropyl acetate; water for 0.0833333 - 0.166667h; pH=2.0 - 8; | 88% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With (1R,2S)-2-Amino-1,2-diphenylethanol In ethyl acetate at 20℃; for 2h; Reflux; Resolution of racemate; | 56% |
Multi-step reaction with 2 steps 1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 2: hydrogenchloride / ethyl acetate; water / pH 3 View Scheme | |
Multi-step reaction with 2 steps 1: ethanol / 0.08 h / Resolution of racemate; Reflux 2: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme |
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
A
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
B
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
Conditions | Yield |
---|---|
With potassium hydroxide; potassium permanganate at 60 - 90℃; for 1.5h; | A 51% B 17% |
With potassium hydroxide; potassium permanganate In water at 60 - 90℃; for 1.5h; | A 51% B 17% |
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.13,7]decane-1-acetic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With potassium permanganate; water; potassium hydroxide at 60 - 90℃; for 1.5h; | 51% |
With potassium permanganate; potassium hydroxide at 90℃; | 49% |
With potassium permanganate; tetrabutylammomium bromide; potassium hydroxide In water at 20 - 25℃; | 18.6 g |
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 2: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 3: 4.07 g / K2CO3 / dimethylformamide / 19 h 4: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride; water / acetic acid / 80 °C 2: hydrogen; palladium 10% on activated carbon / acetic acid 3: triethylamine / methanol 4: potassium permanganate; potassium hydroxide / 90 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 2.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 3.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 3.2: 0 - 5 °C 4.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 2: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 3: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 4: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 2: 4.07 g / K2CO3 / dimethylformamide / 19 h 3: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen; palladium 10% on activated carbon / acetic acid 2: triethylamine / methanol 3: potassium permanganate; potassium hydroxide / 90 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 2.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 2.2: 0 - 5 °C 3.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 2: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 3: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme |
1-adamantanemethanol
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 2: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 3: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 4: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 5: 4.07 g / K2CO3 / dimethylformamide / 19 h 6: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 1.2: 0 - 5 °C 2.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 3.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 4.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 5.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 5.2: 0 - 5 °C 6.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 3.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 4.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 5.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 6.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium bromide / dichloromethane; water / 12 h / 5 - 30 °C 2.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C 3.1: sulfuric acid / 45 - 50 °C 3.2: 2 h / 20 - 35 °C 4.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr 5.1: sulfuric acid / 110 - 112 °C 6.1: sulfuric acid; nitric acid / 10 - 25 °C 7.1: sodium hydroxide / 5 h / 25 - 30 °C View Scheme |
1-Adamantanecarboxylic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 100 percent / diethyl ether; hexane; methanol / 3 h / 20 °C 2: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 3: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 4: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 5: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 6: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 7: 4.07 g / K2CO3 / dimethylformamide / 19 h 8: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: thionyl chloride / 3 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 3.2: 0 - 5 °C 4.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 5.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 6.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 7.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 7.2: 0 - 5 °C 8.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: thionyl chloride / 4 h / Reflux 2.1: sodium / Petroleum ether / 20 °C 2.2: 20 °C 2.3: 6 h / Reflux 3.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 4.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 5.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 6.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 7.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C 8.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
1-Adamantanecarbaldehyde
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 2: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 3: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 4: 4.07 g / K2CO3 / dimethylformamide / 19 h 5: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydrogensulfite / 0 - 60 °C 2: hydrogenchloride; water / acetic acid / 80 °C 3: hydrogen; palladium 10% on activated carbon / acetic acid 4: triethylamine / methanol 5: potassium permanganate; potassium hydroxide / 90 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 2.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 3.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 4.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 4.2: 0 - 5 °C 5.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 5 steps 1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 2: hydrogenchloride; water / acetic acid / 18 h / 80 °C 3: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 4: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 5: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium hydrogen sulfate / water; methanol / 5 - 77 °C 2.1: sulfuric acid / 45 - 50 °C 2.2: 2 h / 20 - 35 °C 3.1: 10 wt% Pd(OH)2 on carbon; acetic acid; hydrogen / methanol / 760.05 Torr 4.1: sulfuric acid / 110 - 112 °C 5.1: sulfuric acid; nitric acid / 10 - 25 °C 6.1: sodium hydroxide / 5 h / 25 - 30 °C View Scheme |
methyl adamantane-1-carboxylate
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / LiAlH4 / tetrahydrofuran / 1.5 h / 0 - 20 °C 2: 98 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C 3: 65 percent / NaHSO3 / H2O; methanol / 16 h / Heating 4: 78 percent / aq. HCl; AcOH / 18 h / 80 °C 5: H2; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr 6: 4.07 g / K2CO3 / dimethylformamide / 19 h 7: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2.1: potassium bromide; sodium hydrogencarbonate / dichloromethane / 0.25 h / 0 - 5 °C 2.2: 0 - 5 °C 3.1: sodium hydrogensulfite / methanol; water / 0 - 55 °C 4.1: hydrogenchloride; acetic acid; water / 20 - 95 °C 5.1: acetic acid; hydrogen; 10% palladium hydroxide on charcoal / methanol / 20 °C 6.1: sodium hydroxide / water / 0.25 h / 0 - 5 °C 6.2: 0 - 5 °C 7.1: potassium permanganate; potassium hydroxide; tetrabutylammomium bromide / water / 20 - 25 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 3.1: sodium hydrogensulfite / methanol; water / 18 h / 0 - 20 °C / Reflux 4.1: hydrogenchloride; water / acetic acid / 18 h / 80 °C 5.1: hydrogen; 20% palladium hydroxide-activated charcoal / methanol; acetic acid / 18 h / 2585.81 Torr 6.1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 7.1: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme |
(S)-(+)-β-amino-1-adamantaneacetic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 4.07 g / K2CO3 / dimethylformamide / 19 h 2: 51 percent / KMnO4; aq. KOH / 1.5 h / 60 - 90 °C View Scheme | |
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 10 - 25 °C 2: sodium hydroxide / 5 h / 25 - 30 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate pH=3; |
N-tert-butoxycarbonyl-2-(3-hydroxy-1-adamantyl)-D-glycine
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; isobutyl chloroformate / tetrahydrofuran / 1.5 h / -8 °C 1.2: 18 h / -8 - 25 °C 2.1: ethyl acetate / 17.42 h / 20 - 70 °C / Resolution of racemate 3.1: hydrogenchloride / ethyl acetate; water / pH 3 View Scheme | |
Multi-step reaction with 3 steps 1.1: dicyclohexyl-carbodiimide / dimethyl sulfoxide / 5 h / 20 °C 1.2: 53 h / 20 - 50 °C 1.3: 2 h 2.1: ethanol / 0.08 h / Resolution of racemate; Reflux 3.1: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme |
(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / methanol 2: potassium permanganate; potassium hydroxide / 90 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere 2: water; potassium permanganate; potassium hydroxide / 1.5 h / 60 - 90 °C View Scheme |
2-(adamantan-1-yl)-2-aminoacetic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 2: potassium permanganate; potassium hydroxide / 2 h / 90 °C 3: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
1-acetyladamantane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 2: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 3: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 4: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 5: potassium permanganate; potassium hydroxide / 2 h / 90 °C 6: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
oxo-tricyclo[3.3.1.13,7]decan-1-yl-acetic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 2: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 3: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 4: potassium permanganate; potassium hydroxide / 2 h / 90 °C 5: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
1-adamantyl-2-hydroxyiminoacetic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 2: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 3: potassium permanganate; potassium hydroxide / 2 h / 90 °C 4: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
1-Adamantanecarbonyl chloride
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium / Petroleum ether / 20 °C 1.2: 20 °C 1.3: 6 h / Reflux 2.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / water; tert-butyl alcohol / 3 h / 40 - 45 °C 3.1: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h 4.1: sodium hydroxide; nickel aluminum / ethanol / 8 h / 50 °C 5.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / pH 10 6.1: potassium permanganate; potassium hydroxide / 2 h / 90 °C 7.1: (1R,2S)-2-Amino-1,2-diphenylethanol / ethyl acetate / 2 h / 20 °C / Reflux; Resolution of racemate View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 2.1: water / 0.17 h / 0 - 2 °C 2.2: 14.5 h / -4 - 80 °C 3.1: hydrogenchloride; water / 1 h / 24 - 80 °C 3.2: 12 h / 80 - 82 °C 4.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 5.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 5.2: 2.08 h / 3 - 26 °C 5.3: 12 h / 40 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: water / 0.17 h / 0 - 2 °C 1.2: 14.5 h / -4 - 80 °C 2.1: hydrogenchloride; water / 1 h / 24 - 80 °C 2.2: 12 h / 80 - 82 °C 3.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 4.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 4.2: 2.08 h / 3 - 26 °C 4.3: 12 h / 40 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; water / 1 h / 24 - 80 °C 1.2: 12 h / 80 - 82 °C 2.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 3.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 3.2: 2.08 h / 3 - 26 °C 3.3: 12 h / 40 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 2.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 2.2: 2.08 h / 3 - 26 °C 2.3: 12 h / 40 °C View Scheme |
di-tert-butyl dicarbonate
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Stage #1: (2S)-amino[3-chlorotricyclo[3.3.1.13'7]dec-1-yl]ethanoic acid hydrochloride With water; potassium carbonate In tetrahydrofuran at 3 - 10℃; for 0.166667h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 3 - 26℃; for 2.08333h; Stage #3: With water at 40℃; for 12h; | 1.16 g |
3-hydroxyadamantane-1-carboxylic acid
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 2.5 h / 0 - 31 °C 1.2: 14.5 h / 0 - 30 °C 1.3: 1 h / 0 - 10 °C 2.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C 3.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 4.1: water / 0.17 h / 0 - 2 °C 4.2: 14.5 h / -4 - 80 °C 5.1: hydrogenchloride; water / 1 h / 24 - 80 °C 5.2: 12 h / 80 - 82 °C 6.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 7.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 7.2: 2.08 h / 3 - 26 °C 7.3: 12 h / 40 °C View Scheme |
1-hydroxy-3-hydroxymethyladamantane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium bromide; sodium hydrogencarbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / dichloromethane; water / 0 - 5 °C 2.1: sodium hydrogensulfite / water / 0.17 h / 0 - 2 °C 3.1: water / 0.17 h / 0 - 2 °C 3.2: 14.5 h / -4 - 80 °C 4.1: hydrogenchloride; water / 1 h / 24 - 80 °C 4.2: 12 h / 80 - 82 °C 5.1: acetic acid; palladium(II) hydroxide; hydrogen / methanol / 5 h / 48 - 52 °C / 2625.26 - 3000.3 Torr 6.1: potassium carbonate; water / tetrahydrofuran / 0.17 h / 3 - 10 °C 6.2: 2.08 h / 3 - 26 °C 6.3: 12 h / 40 °C View Scheme |
1-acetyl-3-chloroadamantane
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: potassium hydroxide / water / 6 h / Reflux 2: potassium hydroxide; potassium permanganate / water; tert-butyl alcohol / 4.5 h / 35 - 45 °C 3: sodium hydroxide; hydroxylamine hydrochloride / water / 2 h / 0 - 5 °C / pH 7 4: sodium hydroxide; nickel-aluminum alloy / water / 50 °C 5: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10 6: ethanol / 0.08 h / Resolution of racemate; Reflux 7: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / water; tetrahydrofuran / 12 h / 20 °C / pH 10 2: ethanol / 0.08 h / Resolution of racemate; Reflux 3: hydrogenchloride / water; ethyl acetate / pH 2 View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water; ethyl acetate pH=2; | 0.96 g |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile Solvent; Large scale; | 98.1% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h; | 46% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
cis-2-azabicyclo[3.1.0]hexane hydrochloride
(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h; | 97.5% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
bis(pentafluorophenyl)carbonate
Conditions | Yield |
---|---|
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h; Stage #2: bis(pentafluorophenyl)carbonate In ethyl acetate at 25℃; for 2h; | 93.1% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
D-cis-4,5-methanoprolineamide methanesulfonic acid salt
(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h; | 93% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
2,2'-dipyridyl carbonate
Conditions | Yield |
---|---|
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With triethylamine In ethyl acetate at 25℃; for 0.666667h; Stage #2: 2,2'-dipyridyl carbonate In ethyl acetate at 25℃; for 3h; | 92.2% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(1S)-α-amino-3-hydroxyadamantane-acetic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane; isopropyl alcohol at 10 - 35℃; for 8h; | 90% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
bis-(p-nitrophenyl) carbonate
Conditions | Yield |
---|---|
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid With dmap; triethylamine In N,N-dimethyl-formamide at 25℃; for 0.666667h; Stage #2: bis-(p-nitrophenyl) carbonate In N,N-dimethyl-formamide at 70℃; for 5h; Solvent; | 90% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
1-hydroxy-pyrrolidine-2,5-dione
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25℃; for 1h; | 90% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
Conditions | Yield |
---|---|
Stage #1: (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid; (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0℃; for 0.5h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0 - 20℃; for 4.5h; | 89.3% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.13'7]dec-1-yl)-2-oxoethyl]carbamate
Conditions | Yield |
---|---|
With TEA; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 85% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 85% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
1,4-diaza-bicyclo[2.2.2]octane
(<αS)-<α[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxytricyclo[3.3.1.137] decane-1-acetic acid DABCO salt
Conditions | Yield |
---|---|
In Isopropyl acetate; water; ethyl acetate at 20℃; | 79% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
L-trans-4,5-methanoprolineamide methanesulfonic acid salt
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h; | 79% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
D-trans-4,5-methanoprolineamide methanesulfonic acid salt
(S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile for 3h; | 71% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(1RS,5SR)-2-azabicyclo[3.1.0]hexane hydrochloride
A
(2R,3S)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
B
(2S,3R)-1-[(2S)-N-Boc-2-(3-hydroxyadamant-1-yl)glycin]-2,3-methanopyrrolidine
Conditions | Yield |
---|---|
With 4-methyl-morpholine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dichloromethane at 20℃; for 20h; | A 27.4% B 40.6% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid
Conditions | Yield |
---|---|
With potassium permanganate; potassium hydroxide In water at 60 - 85℃; for 1.5h; | 25% |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
N-(cyanomethyl)ethylamine
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(methylamino)acetonitrile
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: EDAC; HOAt; Et3N / CH2Cl2 2: TFA / CH2Cl2 View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: EDAC; HOAt; Et3N / CH2Cl2 2: TFA / CH2Cl2 View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C 3: 82 percent / imidazole; pyridine; POCl3 / -20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate; acetic acid butyl ester / 17.5 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1.5 h / 0 °C 2.2: 20 - 25 °C / pH > 10 View Scheme | |
Multi-step reaction with 2 steps 1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h 2.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C 2.2: 18 h / 20 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(S)-N-Boc-3-fluoroadamantylglycine-L-cis-4,5-methanoprolinamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2: 94 percent / diethylaminosulfur trifluoride / CH2Cl2 / 0.25 h / -78 °C 3: 72 percent / CH2Cl2 / 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.67 h / -30 °C / Inert atmosphere 4: dichloromethane / 0.5 h / 20 °C View Scheme |
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid
(S)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile TFA salt
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 85 percent / EDAC; HOBT; TEA / dimethylformamide / 20 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 1 h 2.2: 92 percent / aq. KOH / methanol / 18 h / 20 °C 3.1: 95 percent / CH2Cl2 / 2.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: benzotriazol-1-ol / dichloromethane / 0.08 h / -5 - 0 °C 1.2: 15.5 h / -7 - 10 °C 2.1: pyridine; trifluoroacetic anhydride / tetrahydrofuran / 6.33 h / -3 - 15 °C 2.2: 7 - 15 °C / pH 10 - 10.5 3.1: dichloromethane / -5 - 2 °C View Scheme | |
Multi-step reaction with 4 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 - 0 °C / Inert atmosphere 3: 1H-imidazole; pyridine; trichlorophosphate / 0.75 h / -30 °C / Inert atmosphere 4: water / dichloromethane / 1.5 h / 0 °C View Scheme |
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