(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

Base Information

Chemical Name:(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide
CAS No.:220569-44-8
Molecular Formula:C₂₇H₃₀N₂O₄S
Molecular Weight:478.612
Hs Code.:

Synonyms:(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

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Chemical Property of (2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

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Technology Process of (2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

There total 7 articles about (2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide 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: 73.0%

: 220569-42-6
(2S,3S)-2-(3-benzenesulfonylamino-3-benzyl-2-oxo-pyrrolidin-1-yl)-4-phenylbutyric acid methyl ester

: 220569-44-8
(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

Guidance literature:: With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at -5 - 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

: 220569-44-8
(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

Guidance literature:: Multi-step reaction with 7 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: 697 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

5.1: 91 percent / hydrogen / Pd/C / ethanol

6.1: 80 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

7.1: 73 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / -5 - 25 °C

With pyridine; dmap; sodium tetrahydroborate; 4 A molecular sieve; hydrogen; sodium acetate; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; calcium chloride; 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 / 7.1: Reduction;
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

: 220569-44-8
(2S,3S)-N-[3-benzyl-1-(1-hydroxymethyl-3-phenylpropyl)-2-oxo-pyrrolidin-3-yl]-benzene-sulfonamide

Guidance literature:: Multi-step reaction with 5 steps

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

2: 697 mg / 1-hydroxybenzotriazole / toluene / 16 h / Heating

3: 91 percent / hydrogen / Pd/C / ethanol

4: 80 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 25 °C

5: 73 percent / NaBH₄; CaCl₂ / ethanol; tetrahydrofuran / -5 - 25 °C

With pyridine; dmap; sodium tetrahydroborate; 4 A molecular sieve; hydrogen; sodium acetate; sodium cyanoborohydride; benzotriazol-1-ol; calcium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: Alkylation / 2: Cyclization / 3: Hydrogenolysis / 4: Substitution / 5: Reduction;
DOI:10.1016/S0968-0896(98)80022-9