(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

Base Information

Chemical Name:(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid
CAS No.:1416358-97-8
Molecular Formula:C₂₅H₃₀N₂O₅
Molecular Weight:438.524
Hs Code.:

Synonyms:(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

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Chemical Property of (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

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Technology Process of (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

There total 2 articles about (3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

: 1416358-95-6
tert-butyl-benzyl ((3S,4R)-4-(hydroxymethyl)-2-oxo-1-((S)-1-phenylethyl)pyrrolidin-3-yl)carbamate

: 1416358-97-8
(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide; In dichloromethane; at 0 ℃; for 0.166667h; pH=8.6;
DOI:10.1007/s00726-012-1275-1

Reference yield:

: (3S,4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1S)-1-phenylethyl]-3-{[phenylmethylene]amino}pyrrolidin-2-one

: 1416358-97-8
(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 3 h

3: ammonium fluoride / methanol / 6 h / Reflux

4: 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium bromide; sodium hypochlorite / dichloromethane / 0.17 h / 0 °C / pH 8.6

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; ammonium fluoride; sodium hypochlorite; sodium tetrahydroborate; triethylamine; sodium bromide; In methanol; dichloromethane;
DOI:10.1007/s00726-012-1275-1

Reference yield:

: 1416358-97-8
(3R,4S)-4-(benzyl(tert-butoxycarbonyl)amino)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid

: (3S,4R)-N-benzyl-4-(benzyl((3S,4R)-4-(methoxycarbonyl)-2-oxo-1-((S)-1-phenylethyl)pyrrolidin-3-yl)carbamoyl)-2-oxo-1-((S)-1-phenylethyl)pyrrolidin-3-aminium 2,2,2-trifluoroacetate

Guidance literature:: Multi-step reaction with 2 steps

1: bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: dichloromethane / 1 h / 20 °C

With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In dichloromethane;
DOI:10.1007/s00726-012-1275-1