(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Base Information

Chemical Name:(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester
CAS No.:220569-47-1
Molecular Formula:C₁₆H₂₂N₂O₅S
Molecular Weight:354.427
Hs Code.:

Synonyms:(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

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Chemical Property of (2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

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Technology Process of (2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

There total 6 articles about (2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester 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: 61.0%

: 124-63-0
methanesulfonyl chloride

: 220569-39-1
(2S,3S)-2-(3-amino-3-benzyl-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

: 220569-47-1
(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 - 25 ℃;
DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

: 191980-50-4
(2S,4S)-4-benzyl-2-tert-butyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

: 220569-47-1
(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: 77 percent / tetrahydrofuran; toluene / 16 h / -78 - 25 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2.2: 95 percent / Me₂S / CH₂Cl₂; methanol / -78 - 25 °C

3.1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

4.1: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

5.1: 90 percent / hydrogen / Pd/C / ethanol / 17 h

6.1: 61 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

With pyridine; dmap; 4 A molecular sieve; hydrogen; sodium acetate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1.1: Metallation / 1.2: Alkylation / 2.1: ozonolysis / 2.2: Reduction / 3.1: Alkylation / 4.1: Cyclization / 5.1: Hydrogenolysis / 6.1: Substitution;
DOI:10.1016/S0968-0896(98)80022-9

Reference yield:

: 220569-30-2
(2S,4R)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid benzyl ester

: 220569-47-1
(2S,3S)-2-(3-benzyl-3-methylsulfonylamino-2-oxo-pyrrolidin-1-yl)-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: NaOAc; 4 Angstroem molecular sieves; NaCNBH₃ / methanol / 25 °C

2: 610 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

3: 90 percent / hydrogen / Pd/C / ethanol / 17 h

4: 61 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

With pyridine; dmap; 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; palladium on activated charcoal; In methanol; ethanol; dichloromethane; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis / 4: Substitution;
DOI:10.1016/S0968-0896(98)80022-9