Water → N-(benzyloxycarbonyl)-3(S)-phenylthiomethy-beta-alanine tert-butyl ester

HRID 843723Notes

Reaction equation

HRID 843723 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]([O:14][C:15](=[O:31])[CH2:16][C@@H:17]([CH2:29]I)[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])([CH3:13])([CH3:12])[CH3:11].O>CN(C)C=O>[C:10]([O:14][C:15](=[O:31])[CH2:16][C@@H:17]([CH2:29][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 10971821N-(benzyloxycarbonyl)-3(S)-iodomethy-beta-alanine tert-butyl ester

Product 1

HCID 86584058N-(benzyloxycarbonyl)-3(S)-phenylthiomethy-beta-alanine tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophenol (0.15 ml) in N,N-dimethylformamide (6 ml) was added NaH (58 mg) under ice cooling. After stirring at room temperature for 30 minutes, N-(benzyloxycarbonyl)-3(S)-iodomethy-β-alanine tert-butyl ester (0.6 g) was added and stirred for additional 1 hour. The mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5% (EtOAc/n-hexane) to give N-(benzyloxycarbonyl)-3(S)-phenylthiomethy-β-alanine tert-butyl ester (0.64 g) as an pale yellow oil.

Workup

  1. stirringstirred for additional 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 5% (EtOAc/n-hexane)

Sources & evidence

ORD record
ord-134b4900c14b4de1ac75f9a5b22f12e6
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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