Trifluoroacetic acid → 2-{2-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-4-fluoro-phenyldisulfanyl]-5-fluorobenzoylamino}-4-methyl-pentanoic acid

HRID 1378469Notes

Reaction equation

HRID 1378469 reaction equation
C(OC(=O)C(N([S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:31](=[O:45])[NH:32][CH:33]([C:38]([O:40]C(C)(C)C)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])C(=O)C1C=C(F)C=CC=1)CC(C)C)(C)(C)C.F[C:48](F)(F)[C:49]([OH:51])=[O:50]>ClCCl.C1(OC)C=CC=CC=1>[C:49]([CH:48]([NH:32][C:31]([C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:31]([NH:32][CH:33]([CH2:34][CH:35]([CH3:36])[CH3:37])[C:38]([OH:40])=[O:39])=[O:45])=[O:45])[CH2:37][CH:35]([CH3:34])[CH3:36])([OH:51])=[O:50]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 882885452-[[2-(1-Tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino]-4-methyl pentanoic acid tert-butyl ester

Product 1

HCID 69170712-{2-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-4-fluoro-phenyldisulfanyl]-5-fluorobenzoylamino}-4-methyl-pentanoic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

The general method of Preparation 20 was followed using [S-(R*,R*)]-2-[2-[[2-(1-tert-butoxycarbonyl-3-methylbutylcarbamoyl)-4-fluorophenyldisulfanyl]-5-fluorobenzoylamino]-4-methylpentanoic acid tert-butyl ester (1.8 g, 2.6 mmol) in 20 mL dichloromethane, anisole (2 mL), and 20 mL trifluoroacetic acid. The crude product was recrystallized from methanol/water to afford 0.9 g of the title compound.

Workup

  1. customThe general method of Preparation 20
  2. customThe crude product was recrystallized from methanol/water

Sources & evidence

ORD record
ord-3dbba61a4973455080079705d7dba8fd
Source dataset
uspto-grants-1997_09
Patent number
US05668162

Reaction notes

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