Trifluoroacetic acid → alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclopentaneacetic acid

HRID 1068156Notes

Reaction equation

HRID 1068156 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]=[CH:24][CH:23]=4)[CH2:20][N:19]([C@H:28]([CH:41]4C[CH2:45][CH2:44][CH2:43][CH2:42]4)[C:29]([O:31]CC4C=CC(OC)=CC=4)=[O:30])[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.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>>[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:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:20][N:19]([C@H:28]([CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45]4)[C:29]([OH:31])=[O:30])[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

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57253738alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)4-(S)-phenyl-pyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester

Product 1

HCID 20664157alpha-(R)-(3-(S)-((4-Benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclopentaneacetic acidYield 115.5%

Procedure

To 26.5 mg of α-(R)-(3-(S)-((4-benzoimidazol-1-yl-piperidin-1-yl)methyl)-4-(S)-phenyl-pyrrolidin-1-yl)- cyclohexaneacetic acid, 4-methoxy-benzyl ester (from Step D) was added 0.2 mL of anisole and 2 mL of TFA. After stirring at room temperature for 1.5 hours, concentrated under pressure. The residue was purified by flash chromatography eluting with 10% CH3OH in CH2Cl2, then 15% CH3OH/1% NH4OH in CH2Cl2 to give 24 mg of the title compound as a solid. 1H NMR (400 MHz, CDCl3): δ1.17-3.73 (m, 28H), 4.35 (m, 1H), 7.27 (m, 3H), 7.46(m, 4H), 7.55(s. 1H). 7.65(d, J=7.4 Hz, 1H), 8.17(d, J=5.0 Hz, 1H). ESI-MS 510 (M+H); HPLC A: 1.67 min.

Workup

  1. concentrationconcentrated under pressure
  2. customThe residue was purified by flash chromatography
  3. washeluting with 10% CH3OH in CH2Cl2

Sources & evidence

ORD record
ord-a481e0d3974740a09eb7bfc6e615f338
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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