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

HRID 3698Notes

Reaction equation

HRID 3698 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]([F:20])[C:15]=1[S:21][S:22][C:23]1[C:28]([F: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])[CH:33]([CH3:36])[CH2:34][CH3:35])[CH:8]([CH3:11])[CH2:9][CH3:10])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[C:37]([CH:32]([NH:31][C:30]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[S:22][S:21][C:15]1[C:16]([F:20])=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][CH:7]([CH:8]([CH3:11])[CH2:9][CH3:10])[C:6]([OH:46])=[O:5])=[O:45])=[O:44])[CH:33]([CH3:36])[CH2:34][CH3:35])([OH:39])=[O:38]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 761258512-[2-[2-(1-Tert-butoxycarbonyl-2-methyl-butylcarbamoyl)-6-fluorophenyldisulfanyl]-3-fluoro-benzoylamino]-3-methylpentanoic acid tert butyl ester

Product 1

HCID 537920672-{2-[2-(1-Carboxy-2-methyl-butylcarbamoyl)-6-fluoro-phenyldisulfanyl]-3-fluoro-benzoylamino}-3-methyl-pentanoic acidYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [S-(R*,R*)]-2-[2-[2-(1-tert-butoxycarbonyl-2-methyl-butylcarbamoyl)-6-fluorophenyldisulfanyl]-3-fluoro- benzoylamino]-3-methylpentanoic acid tert butyl ester (0.6 g ,0.8 mmol) and anisole (1 ml) in 10 mL dichloromethane at 0° C., was added dropwise 10 mL trifluoroacetic acid. The mixture was allowed to warm to ambient temperature. After 4 hours, 5 mL toluene was added and the solvents were removed in vacuo. The crude product was recrystallized from methanol/water to yield 0.2 g of the title compound, mp 188°-190° C.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe crude product was recrystallized from methanol/water

Sources & evidence

ORD record
ord-58247be6c9cf4f31b764ec27ffb99a3b
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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