Sodium Hydroxide → HCID 69462061, compound

HRID 1264375Notes

Reaction equation

HRID 1264375 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:4].[OH-].[Na+].OS([O-])(=O)=O.[K+].CCOC(C)=O>C1COCC1.CCO>[C:33]([O:32][C:30]([N:6]1[CH2:7][C@H:8]([S:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11420714(2S,4R)-4-Tritylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 86585043ethylacetate KHSO4

Product 1

HCID 69462061HCID 69462061, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 14.7 g (29.2 mmol) (2S,4R)-4-Tritylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester was dissolved in 660 ml THF/EtOH (1:1) and treated at RT with 58.4 ml (58.4 mmol) aqueous 1 N NaOH. After 2 h the reaction was poured into aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl solution and dried over Na2SO4 to give 14.8 g (quantitativ) of (2S,4R)-4-Tritylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester. MS: 488 (M-H)−.

Workup

  1. washThe organic phases were washed with aqueous 10% NaCl solution
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-4acbc038c35e47fd8c1034fc08369722
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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