Trifluoroacetic acid → 2-{5-Acetylamino-2-[4-acetylamino-2-(1-carboxy-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid

HRID 3704Notes

Reaction equation

HRID 3704 reaction equation
C([O:5][C:6](=[O:52])[CH:7]([NH:12][C:13](=[O:51])[C:14]1[CH:19]=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[CH:17]=[CH:16][C:15]=1[S:24][S:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:35])[CH3:34])=[CH:28][C:27]=1[C:36](=[O:50])[NH:37][CH:38]([C:43]([O:45]C(C)(C)C)=[O:44])[CH2:39][CH:40]([CH3:42])[CH3:41])[CH2:8][CH:9]([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([S:24][S:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:35])[CH3:34])=[CH:28][C:27]=2[C:36](=[O:50])[NH:37][CH:38]([C:43]([OH:45])=[O:44])[CH2:39][CH:40]([CH3:41])[CH3:42])=[C:14]([CH:19]=1)[C:13]([NH:12][CH:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]([OH:52])=[O:5])=[O:51])(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 542825182-{5-Acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 69170732-{5-Acetylamino-2-[4-acetylamino-2-(1-carboxy-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]2-{5-acetylamino-2-[4-acetylamino-2-(1-tert-butoxycarbonyl-3-methyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-4-methyl-pentanoic acid tert-butyl ester (0.2 g, 0.2 mmol) from Example 44, 10 mL dichloromethane, and 10 mL trifluoroacetic acid. The crude product was recrystallized from dimethylformamide/water to afford 0.1 g of the title compound, mp 241°-242° C.

Workup

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

Sources & evidence

ORD record
ord-264b85044b034d0ba81c2947a44108fd
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Reaction notes

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