Trifluoroacetic acid → alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid

HRID 1068166Notes

Reaction equation

HRID 1068166 reaction equation
[F:1][C:2]1[CH:47]=[CH:46][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]4[C@@H:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:19][N:18]([C@H:27]([CH:40]5[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]5)[C:28]([O:30]CC5C=CC(OC)=CC=5)=[O:29])[CH2:17]4)[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[F:1][C:2]1[CH:47]=[CH:46][C:5]2[N:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]4[C@@H:20]([C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:19][N:18]([C@H:27]([CH:40]5[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]5)[C:28]([OH:30])=[O:29])[CH2:17]4)[CH2:11][CH2:10]3)[CH:7]=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86757026alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester

Product 1

HCID 20664142alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acidYield 90.1%

Procedure

The title compound was prepared from 41 mg of α-(R)-(3-(S)-((4-(5-fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenyl-pyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (from Step D) and 4 mL of TFA, 0.3 mL of anisole, using a procedure analogous to that described in Example 95, Step E to provide 30 mg of the title compound as a solid. ESI-MS 519 (M+H); TPLC A: 1.65 min.

Sources & evidence

ORD record
ord-91a87a1b53104dbab739208fe572b939
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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