Trifluoroacetic acid → 2-{2-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-6-methyl-phenyldisulfanyl]-3-methyl-benzoylamino}-4-methyl-pentanoic acid

HRID 3702Notes

Reaction equation

HRID 3702 reaction equation
C([O:5][C:6](=[O:46])[CH:7]([NH:12][C:13](=[O:45])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[S:21][S:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[C:30](=[O:44])[NH:31][CH:32]([C:37]([O:39]C(C)(C)C)=[O:38])[CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:8][CH:9]([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:37]([CH:32]([NH:31][C:30]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[S:22][S:21][C:15]1[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][CH:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[C:6]([OH:46])=[O:5])=[O:45])=[O:44])[CH2:33][CH:34]([CH3:35])[CH3:36])([OH:39])=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 764140442-[2-[2-(1-tert-Butoxycarbonyl-3-methylbutylcarbamoyl)-6-methyl-phenyldisulfanyl]-3-methylbenzoylamino]-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 867523522-{2-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-6-methyl-phenyldisulfanyl]-3-methyl-benzoylamino}-4-methyl-pentanoic acidYield 54.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-6-methyl-phenyldisulfanyl]-3-methylbenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (0.9 g, 1.3 mmol) from Example 32, 10 mL dichloromethane, and 10 mL trifluoroacetic acid. The crude product was recrystallized from dimethylformamide/water to afford 0.4 g of the title compound, mp 210°-211° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-c6ce76bad70b40cc9115ea80cc9c91d4
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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