Trifluoroacetic acid → 4-[2-[2-(3-Carboxypropylcarbamoyl)phenyldisulfanyl]benzoylamino] butanoic acid

HRID 1378795

Reaction equation

HRID 1378795 reaction equation
CC([O:5][C:6](=[O:40])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19][S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([NH:29][CH2:30][CH2:31][CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])=[O:28])=[O:12])(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>ClCCl>[C:22]1([C:27]([NH:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:28])[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:20][S:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([NH:10][CH2:9][CH2:8][CH2:7][C:6]([OH:40])=[O:5])=[O:12]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 867512584,4'-[Dithiobis(2,1-phenylenecarbonylimino)]bis butanoic acid bis (1,1-dimethylethyl)ester

Product 1

HCID 4688864-[2-[2-(3-Carboxypropylcarbamoyl)phenyldisulfanyl]benzoylamino] butanoic acidYield 139.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the procedure described in Example 50 using 4,4'-[dithiobis(2,1-phenylenecarbonylimino)]bis butanoic acid bis (1,1-dimethylethyl) ester (0.5 g, 0.9 mmol) from Example 43, 10 mL dichloromethane, 10 mL trifluoroacetic acid, and 1 mL anisole. The crude product was recrystallized from methanol/dimethylformamide/water to afford 0.6 g of the title compound, mp 165°-166° C.

Workup

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

Sources & evidence

ORD record
ord-03ab817d720446708337ba226b13df4e
Source dataset
uspto-grants-1997_09
Patent number
US05668291

Linked notes

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