Toluene → HCID 21311016, compound

HRID 1378468Notes

Reaction equation

HRID 1378468 reaction equation
C([O:5][C:6](=[O:48])[CH:7]([NH:12][C:13](=[O:47])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[S:22][S:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[C:32](=[O:46])[NH:33][CH:34](OC(C)(C)C)[C:35](=C=O)[CH:36]([CH3:38])[CH3:37])[CH2:8][CH:9]([CH3:11])[CH3:10])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)[C:59]([OH:61])=[O:60].C1(C)C=CC=CC=1>ClCCl>[C:6]([CH:7]([NH:12][C:13]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=1[S:22][S:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=1[C:32]([NH:33][CH:34]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:59]([OH:61])=[O:60])=[O:46])=[O:47])[CH2:8][CH:9]([CH3:11])[CH3:10])([OH:5])=[O:48]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131720197HCID 131720197, compound

Product 1

HCID 21311016HCID 21311016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [S-(R*,R*)-2[2-[2-(1-tert-butoxy-carbonyl-3-methylbutylcarbamoyl)-5-methoxy-phenyldisulfanyl]-4-methoxybenzoylamino]-4-methyl-pentanoic acid tert-butyl ester (1.2 g, 1.7 mmol) and anisole (1 mL) in 10 mL dichloromethane, cooled to about 0° C., was treated dropwise with 10 mL of trifluoroacetic acid. The mixture was allowed to warm to ambient temperature. After 4 hours, 5 mL toluene was added, and the solvents were removed in vacuo. The crude product was recrystallized from methanol/water to yield 0.7 g of the title compound.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe crude product was recrystallized from methanol/water

Sources & evidence

ORD record
ord-4a32cc6bcb8248f38d61b8dee1012e13
Source dataset
uspto-grants-1997_09
Patent number
US05668162

Reaction notes

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