Sodium Hydroxide → HCID 59166768, compound

HRID 1442960Notes

Reaction equation

HRID 1442960 reaction equation
CC[O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:8][N:7]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:5].[OH-].[Na+]>CO>[C:22]([O:21][C:19]([N:7]1[CH2:8][C@@H:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=2)[CH2:10][C@H:6]1[C:4]([OH:5])=[O:3])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59166754HCID 59166754, compound

Product 1

HCID 59166768HCID 59166768, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2S,4S)-4-(4-Bromo-phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (Preparation 5, 120 mg, 0.30 mmol) was dissolved in MeOH (6 ml) and 2M sodium hydroxide was added (0.83 ml, 1.66 mmol). The solution was stirred for 14 h, concentrated and added to 0.5M HCl (50 ml). The aqueous was extracted with CH2Cl2 (50 ml) which was dried (magnesium sulphate) and concentrated. Flash column chromatography (eluting first with CH2Cl2 and then with 95% CH2Cl2/MeOH) gave the acid as a clear liquid (130 mg, 48%).

Workup

  1. concentrationconcentrated
  2. additionadded to 0.5M HCl (50 ml)
  3. extractionThe aqueous was extracted with CH2Cl2 (50 ml) which
  4. dry with materialwas dried (magnesium sulphate)
  5. concentrationconcentrated
  6. washFlash column chromatography (eluting first with CH2Cl2

Sources & evidence

ORD record
ord-e5ee404a7d824fdc9525811b9bc79ee1
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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