benzylamine
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
In dichloromethane at 0 - 5℃; for 0.5h; | 100% |
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate
dimethyl sulfate
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 0 - 30℃; for 1.5h; | 96.28% |
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 4 - 25℃; Inert atmosphere; | 75.8% |
Stage #1: tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate; dimethyl sulfate With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 4 - 25℃; Cooling with ice; Inert atmosphere; Stage #2: With ammonium hydroxide In dichloromethane; water | 75.8% |
benzylamine
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
at 20℃; for 3h; | 90.4% |
benzylamine
(R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Stage #1: (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: benzylamine In tetrahydrofuran at -78 - 20℃; for 1h; | 90% |
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78 - 30℃; for 1h; Inert atmosphere; | 90% |
Stage #1: (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: benzylamine With isobutyl chloroformate In tetrahydrofuran at -78 - 20℃; for 1h; Inert atmosphere; | 90% |
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate
trimethoxonium tetrafluoroborate
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In dichloromethane at 20℃; for 16h; Inert atmosphere; Green chemistry; | 81% |
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate
methyl p-toluene sulfonate
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium hydroxide In toluene at -1 - 2℃; Solvent; Reagent/catalyst; Temperature; | 80% |
With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 20℃; for 3h; Reagent/catalyst; | 60.97g |
With tetrabutylammomium bromide; sodium hydroxide In water at 20℃; for 3h; | 38.5 g |
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 3h; | 38.5 g |
benzylamine
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / -5 °C 1.2: -5 - 0 °C 2.1: potassium hydroxide / dichloromethane / 5 °C 2.2: 5 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: methyl chloroformate; 4-methyl-morpholine / dichloromethane / 0.5 h / 35 °C 1.2: 20 °C 2.1: sodium hydroxide; tetrabutylammomium bromide / toluene; water / 2 - 27 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: isobutyl chloroformate; 4-methyl-morpholine / dichloromethane / 5 °C 1.2: 0 - 5 °C 2.1: potassium hydroxide / 5 °C 2.2: 5 °C View Scheme |
di-tert-butyl dicarbonate
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water / 10 h / 20 - 25 °C 2.1: sodium hydroxide / water / 0.5 h / 0 - 5 °C 2.2: 14 h / 5 - 10 °C 2.3: 0 - 5 °C 3.1: chloroformic acid ethyl ester; 4-methyl-morpholine / dichloromethane / 0.25 h / -15 - -10 °C 3.2: 3 h / -15 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydroxide / water 1.2: 16 h / 20 °C 1.3: pH 3.5 - 4 2.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1 h / -20 - 20 °C 3.1: sodium hydroxide / tetrabutylammomium bromide / dichloromethane; water / 2 h / 5 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; sodium hydroxide / water; tert-butyl alcohol / 11 h / 20 °C 2.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.5 h / 0 - 5 °C 2.2: 20 °C 3.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / -10 - -5 °C 3.2: 20 °C View Scheme |
(R)-N-tert-butoxycarbonyl serine
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 0.5 h / 0 - 5 °C 1.2: 14 h / 5 - 10 °C 1.3: 0 - 5 °C 2.1: chloroformic acid ethyl ester; 4-methyl-morpholine / dichloromethane / 0.25 h / -15 - -10 °C 2.2: 3 h / -15 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / -5 °C 1.2: -5 - 0 °C 2.1: potassium hydroxide / dichloromethane / 5 °C 2.2: 5 °C View Scheme | |
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1 h / -20 - 20 °C 2: sodium hydroxide / tetrabutylammomium bromide / dichloromethane; water / 2 h / 5 - 20 °C View Scheme |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 6 h / 35 °C / pH 6.7 / aq. phosphate buffer 2.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: 1 h / -78 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 7 h / 35 °C / pH 6.7 2: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 1 h / -78 - 30 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium dihydrogenphosphate; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / acetonitrile / 3 h / 20 °C 2.1: 4-methyl-morpholine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 2.2: 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
(R)-N-tert-butoxycarbonyl serine
benzylamine
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate / 3.5 h / 4 - 25 °C / Inert atmosphere 2: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane; water / 4 - 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 4-methyl-morpholine / ethyl acetate / 3.5 h / 4 - 25 °C / Cooling with ice; Inert atmosphere 2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane; water / 4 - 25 °C / Cooling with ice; Inert atmosphere View Scheme |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / tert-butyl methyl ether / 60 - 65 °C 2: tert-butyl methyl ether / 60 - 65 °C View Scheme |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
In tert-butyl methyl ether at 60 - 65℃; Solvent; Temperature; | 9 g |
(R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 120 - 130 °C / Dean-Stark 2: triethylamine / tert-butyl methyl ether / 60 - 65 °C 3: tert-butyl methyl ether / 60 - 65 °C View Scheme | |
Multi-step reaction with 2 steps 1: 4-methyl-morpholine / dichloromethane / 1 h / 0 - 5 °C 2: dichloromethane / 0.5 h / 0 - 5 °C View Scheme |
tert-butyl (R)-4-(methoxymethyl)-2,2-dimethyloxazolidine-3-carboxylate
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: p-toluenesulfonic acid monohydrate / methanol / 5 h / 20 °C 2.1: potassium dihydrogenphosphate; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / acetonitrile / 3 h / 20 °C 3.1: 4-methyl-morpholine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 3.2: 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C 2.1: p-toluenesulfonic acid monohydrate / methanol / 5 h / 20 °C 3.1: potassium dihydrogenphosphate; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite / acetonitrile / 3 h / 20 °C 4.1: 4-methyl-morpholine / tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 - 20 °C / Inert atmosphere View Scheme |
benzylamine
(R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid
A
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
B
tert-butyl-N-[(1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxo-ethyl]carbamate
C
benzylcarbamic acid isobutyl ester
Conditions | Yield |
---|---|
Stage #1: (R)-2-((tert-butoxycarbonyl)amino)-3-methoxypropionic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -10 - 0℃; for 3.5h; Stage #2: benzylamine In dichloromethane at -10 - 15℃; for 2h; Overall yield = 150.3 g; | A n/a B n/a C n/a D n/a E n/a F n/a |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
(R)-2-amino-N-benzyl-3-methoxypropanamide
Conditions | Yield |
---|---|
With hydrogenchloride; water In dichloromethane at 0 - 30℃; for 2h; | 100% |
With hydrogenchloride; water In dichloromethane at 0 - 30℃; for 2h; | 100% |
With hydrogenchloride In dichloromethane; water at 0 - 10℃; for 1h; | 100% |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
trifluoroacetic acid
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | 100% |
tert-butyl [(2R)-1-(benzylamino)-3-methoxy-1-oxopropan-2-yl]carbamate
(R)-2-amino-N-benzyl-3-methoxypropionamide hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In methanol at 50℃; for 2h; | |
With hydrogenchloride In dichloromethane; water for 1h; | n/a |
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