alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic acid, benzyl ester → alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic Acid

HRID 1068158Notes

Reaction equation

HRID 1068158 reaction equation
[N:1]1([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:40][CH:41]4[CH2:44][CH2:43][CH2:42]4)[C:30]([O:32]CC4C=CC=CC=4)=[O:31])[CH2:18]3)[CH2:12][CH2:11]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1>[Pd].CO>[NH4+:1].[OH-:31].[N:1]1([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@H:29]([CH2:40][CH:41]4[CH2:42][CH2:43][CH2:44]4)[C:30]([OH:32])=[O:31])[CH2:18]3)[CH2:14][CH2:15]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 1

HCID 86757025alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic acid, benzyl ester

Product 2

HCID 14923Ammonium HydroxideYield 1%HCID 20664155alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-3-cyclobutylpropionic AcidYield 141.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared from 20 mg of α-(R)-(3-(S)-((4-benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-(3-fluorophenyl) pyrrolidin-1-yl)-3-cyclobutylpropionic acid, benzyl ester (from, step A) and 10 mg of 10% palladium on carbon in 4 mL of MeOH using a procedure analogous to that described in Example 1, Step E, except that the title compound was purified by flash chromatography eluting with 10% CH3OH in CH2Cl2, then 15% CH3OH and 1% NH4OH in CH2Cl2 to give 12 mg of the title compound as solid. ESI-MS 505 (M+H); HPLC A: 1.68 min.

Workup

  1. customwas purified by flash chromatography
  2. washeluting with 10% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-3e61d19eaf94497eac51906a7378758e
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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