1-[3(S)-[[N-(tert.butoxycarbonyl)-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide → N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamide

HRID 742903Notes

Reaction equation

HRID 742903 reaction equation
C(OC([NH:8][C@H:9]([C:12]([NH:14][C@@H:15]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:16]([OH:31])[CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:13])[CH2:10][SH:11])=O)(C)(C)C>FC(F)(F)C(O)=O>[C:27]([NH:26][C:24]([C@@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][N:18]1[CH2:17][C@@H:16]([OH:31])[C@@H:15]([NH:14][C:12](=[O:13])[C@H:9]([CH2:10][SH:11])[NH2:8])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 1

HCID 867462921-[3(S)-[[N-(tert.butoxycarbonyl)-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide

Product 1

HCID 86746294N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamideYield 85.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 930 mg of 1-[3(S)-[[N-(tert.butoxycarbonyl)-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N-tert.butyl-2(S)-piperidinecarboxamide in 7 ml of trifluoroacetic acid was stirred at 20° C. for 1 hour. The mixture was then evaporated to dryness and the residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution. The organic phase was evaporated to give 650 mg of N-tert.butyl-1-[3(S)-[(L-cysteinyl)amino]-2(R)-hydroxy-4-phenylbutyl]-2(S)-piperidinecarboxamide as a colourless gum; MS: m/e [M+H]+.

Workup

  1. customThe mixture was then evaporated to dryness
  2. customthe residue was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  3. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-8f321e2b460f44b2886c024c5314aef9
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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