Sodium Hydroxide → 2-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid

HRID 987938Notes

Reaction equation

HRID 987938 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[C:18]([O:17][C:15]([NH:14][CH:4]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[C:3]([OH:22])=[O:2])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 698535532-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid Methyl Ester

Product 1

HCID 232563352-tert-Butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid methyl ester (2.28 g, 6.93 mmol) in methanol (10 ml) was vigorously stirred at room temperature during the addition of 2N aqueous sodium hydroxide solution (7 ml, 14 mmol). The resulting mixture was stirred at room temperature for 2 hours and then concentrated in vacuo. The residue was diluted with water (65 ml) and the aqueous layer was extracted with diethyl ether (2*50 ml). The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was dried (anhydrous magnesium sulfate) and concentrated in vacuo to give, after purification by flash chromatography on silica gel, (dichloromethane/methanol: 98/2 to 96/4) 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid (2.06 g, 95%) as a pale yellow oil. Mass spectrum, 315 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (65 ml)
  3. extractionthe aqueous layer was extracted with diethyl ether (2*50 ml)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried (anhydrous magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give
  8. customafter purification by flash chromatography on silica gel, (dichloromethane/methanol: 98/2 to 96/4) 2-tert-butoxycarbonylamino-3-(4-fluoro-phenylsulfanyl)-propionic acid (2.06 g, 95%) as a pale yellow oil

Sources & evidence

ORD record
ord-082146754d5144c0a6afcf07ce8a2fd5
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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