HCID 86751305, compound → HCID 86751304, compound

HRID 1379201Notes

Reaction equation

HRID 1379201 reaction equation
C([O:8][C:9]([CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:35])[C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[C@H:16]([CH2:36][C:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][CH:38]=2)[CH2:15]1)=[O:10])C1C=CC=CC=1>CO>[C:9]([CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:35])[C:21]2[CH:26]=[C:25]([C:27]([F:29])([F:28])[F:30])[CH:24]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:22]=2)[C@H:16]([CH2:36][C:37]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[NH:39][CH:38]=2)[CH2:15]1)([OH:10])=[O:8]

Participants

3

Reactant 1

HCID 86751305HCID 86751305, compound

Product 1

HCID 86751304HCID 86751304, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2R)-4-[3-(benzyloxycarbonyl)propyl]-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.15 g), 10% Pd charcoal (15 mg) and methanol (4.5 ml) was stirred for 3 hours under hydrogen atmosphere (1 atm). The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography on a silica gel using chloroform-methanol (5:1) as eluent to give (2R)-4-(3-carboxypropyl)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.067 g) as a powder.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography on a silica gel

Sources & evidence

ORD record
ord-8e9994d3228c474d919a932ce34ad820
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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