Trifluoroacetic acid → alpha-(R)-(3-(S)-((4-(2-Methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid

HRID 1068161Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17][N:16]([C@H:25]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:26]([O:28]CC4C=CC(OC)=CC=4)=[O:27])[CH2:15]3)[CH2:9][CH2:8]2)[C:5]2[CH:44]=[CH:45][CH:46]=[CH:47][C:4]=2[N:3]=1.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][C@@H:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:17][N:16]([C@H:25]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)[C:26]([OH:28])=[O:27])[CH2:15]3)[CH2:11][CH2:12]2)[C:5]2[CH:44]=[CH:45][CH:46]=[CH:47][C:4]=2[N:3]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 57317010alpha-(r)-(3-(s)-((4-(2-Methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(s)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester

Product 1

HCID 20664117alpha-(R)-(3-(S)-((4-(2-Methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acidYield 103.9%

Procedure

The title compound was prepared from 57 mg of α-(R)-(3-(S)-((4-(2-methyl-benzoimidazol-1-yl)piperidin-1-yl)methyl)-4-(S)-phenyl-pyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (from Step C), 4 mL of TFA and 0.3 mL of anisole, using a procedure analogous to that described in Example 95, Step E to provide 48 mg of the title compound as a white solid. ESI-MS 515 (M+H); HPLC A: 1.81 min.

Sources & evidence

ORD record: ord-1efcc57aa9bf43a7bb27222eff73b98e
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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