Citric Acid → HCID 67491029, compound

HRID 1917300Notes

Reaction equation

HRID 1917300 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([C@@:10]1([CH2:24][CH:25]=[O:26])[CH2:14][C:13](=[O:15])[N:12]([C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>CO>[C:3]([O:7][C:8]([C@@:10]1([CH2:24][CH2:25][OH:26])[CH2:14][C:13](=[O:15])[N:12]([C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86664647(3S)-5-Oxo-3-(2-oxoethyl)-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67491029HCID 67491029, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (465 mg) was added to a solution of (3S)-5-oxo-3-(2-oxoethyl)-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.71 g, 8.19 mmol) in methanol at −40° C. After heating to room temperature, a 10% citric acid solution was added to the reaction solution, and the mixture was stirred. The reaction solution was poured into a mixture of ethyl acetate (50 mL) and a 10% citric acid solution (10 mL), followed by extraction with ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (100 mL), and then the organic layers were combined and washed with brine (50 mL×2). The resulting organic layer was dried over anhydrous sodium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→0:1→ethyl acetate-methanol=10:1) to give 2.20 g (81%) of the title compound as a white solid.

Workup

  1. extractiona 10% citric acid solution (10 mL), followed by extraction with ethyl acetate (100 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  3. washwashed with brine (50 mL×2)
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→0:1→ethyl acetate-methanol=10:1)

Sources & evidence

ORD record
ord-b372ebc824904632aa04cdde1ef5edd4
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…