HCID 86757210, compound → HCID 20672354, compound

HRID 1386746Notes

Reaction equation

HRID 1386746 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[C@@H:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[CH2:22][N:21]([C@H:31]([CH2:42][CH:43]4[CH2:46][CH2:45][CH2:44]4)[C:32]([O:34]CC4C=CC=CC=4)=[O:33])[CH2:20]3)[CH2:14][CH2:13]2)[CH:5]=[C:6]([F:8])[CH:7]=1>[Pd].CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:18][C@@H:19]3[C@@H:23]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=4)[CH2:22][N:21]([C@H:31]([CH2:42][CH:43]4[CH2:44][CH2:45][CH2:46]4)[C:32]([OH:34])=[O:33])[CH2:20]3)[CH2:16][CH2:17]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 86757210HCID 86757210, compound

Product 1

HCID 20672354HCID 20672354, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(R)-(3-(S)-((4-(3-(3,5-difluorophenyl)propyl) piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-(cyclobutyl)propanoic acid, benzyl ester (from EXAMPLE 95, Step F) and 20 mg 10% palladium on carbon in MeOH (5 mL) was hydrogenated at 50 psi for 90 min. The reaction mixture was filtered though Celite, the filter cake washed with MeOH, and the filtrate concentrated to afford 31 mg (84%, two steps) of the title compound: ESI-MS 543 (M+H); HPLC A: 2.85 min.

Workup

  1. filtrationThe reaction mixture was filtered though Celite
  2. washthe filter cake washed with MeOH
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-75464a9567ce4e2592199ba5ea2bc9c1
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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