Trifluoroacetic acid → HCID 476349, compound

HRID 1378794Notes

Reaction equation

HRID 1378794 reaction equation
C([O:5][C:6](=[O:56])[CH:7]([NH:18][C:19](=[O:55])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26][S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=[O:54])[NH:35][CH:36]([C:47]([O:49]C(C)(C)C)=[O:48])[CH2:37][CH2:38][CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])[CH2:8][CH2:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>ClCCl>[CH:31]1[CH:30]=[C:29]([C:34]([NH:35][C@H:36]([C:47]([OH:49])=[O:48])[CH2:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[O:54])[C:28]([S:27][S:26][C:21]2[C:20]([C:19]([NH:18][C@H:7]([C:6]([OH:56])=[O:5])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:55])=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 76080001HCID 76080001, compound

Product 1

HCID 476349HCID 476349, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared according to the procedure described in Example 50 using [S-(R*,R*)]-2-{2-[2-(1,4-bis-tert-butoxycarbonyl-butylcarbamoyl)-phenyldisulfanyl]-benzoylamino}-hexanedioic acid di-tert-butyl ester (1.1 g, 1.4 mmol) from Example 37, 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 259°-260° C.

Workup

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

Sources & evidence

ORD record
ord-4da50f6baa534b33b8228ca133c0476d
Source dataset
uspto-grants-1997_09
Patent number
US05668291

Reaction notes

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