Triethylamine → N-[3-(3-Acetylthio-2-methylpropanoyl thio)-2-methyl-propanoyl]-N-cyclopentyl glycine-t-butyl ester

HRID 2164780Notes

Reaction equation

HRID 2164780 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16][SH:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:28]([S:31][CH2:32][CH:33]([CH3:37])[C:34](Cl)=[O:35])(=[O:30])[CH3:29]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]([C:14](=[O:19])[CH:15]([CH3:18])[CH2:16][S:17][C:34](=[O:35])[CH:33]([CH3:37])[CH2:32][S:31][C:28](=[O:30])[CH3:29])[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 13469597N-(3-mercapto-2-methylpropanoyl)-N-cyclopentylglycine t-butyl ester

Product 1

HCID 20037734N-[3-(3-Acetylthio-2-methylpropanoyl thio)-2-methyl-propanoyl]-N-cyclopentyl glycine-t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3 g (0.01M) of N-(3-mercapto-2-methyl propanoyl)-N-cyclopentyl glycine-t-butyl ester, 1.2 g (0.012M) triethylamine in 100 ml methylene chloride was added a solution of 1.8 g (0.01M) of 3-acetylthio-2-methyl propanoyl chloride and stirring continued for 8 hours. It was then washed with water, dried over MgSO4 and evaporated to dryness leaving an oily residue which was purified by HPLC using ethyl acetate--hexane (1:3) as eluent.

Workup

  1. washIt was then washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customleaving an oily residue which
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-e0def9c3adfc4501b7a0d5d5a38a1ede
Source dataset
uspto-grants-1985_03
Patent number
US04507316

Reaction notes

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