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

HRID 3701Notes

Reaction equation

HRID 3701 reaction equation
C([O:5][C:6](=[O:48])[CH:7]([NH:12][C:13](=[O:47])[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[S:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[C:32](=[O:46])[NH:33][CH:34]([C:39]([O:41]C(C)(C)C)=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37])[CH2:8][CH:9]([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>ClCCl>[C:39]([CH:34]([NH:33][C:32]([C:25]1[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=1[S:23][S:22][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:13]([NH:12][CH:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[C:6]([OH:48])=[O:5])=[O:47])=[O:46])[CH2:35][CH:36]([CH3:38])[CH3:37])([OH:41])=[O:40]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 76479708HCID 76479708, compound

Product 1

HCID 69170722-{2-[2-(1-Carboxy-3-methyl-butylcarbamoyl)-4-methoxy-phenyldisulfanyl]-5-methoxybenzoylamino}-4-methyl-pentanoic acidYield 34.7%

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)-4-methoxy-phenyldisulfanyl]-5-methoxybenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (2.4 g, 3.4 mmol) from Example 31, 25 mL dichloromethane, 25 mL trifluoroacetic acid and 2.5 mL anisole. The crude product was recrystallized from methanol/water to afford 0.7 g of the title compound, mp 168°-169° C.

Workup

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

Sources & evidence

ORD record
ord-e25215ee60094b58ac72c52a0aebb599
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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