Trifluoroacetic acid → (R)-[(3S,4S)-3-(4-Benzotriazol-1-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-cyclohexyl-acetic acid

HRID 1068146Notes

Reaction equation

HRID 1068146 reaction equation
Cl.[N:2]1([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH:17]([C@@H:19]1[C@@H:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][N:21]([C@H:30]([CH:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[C:31]([O:33]CC2C=CC(OC)=CC=2)=[O:32])[CH2:20]1)=O.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>C(O)=O>[N:2]1([CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:19]3[C@@H:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:22][N:21]([C@H:30]([CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]4)[C:31]([OH:33])=[O:32])[CH2:20]3)[CH2:13][CH2:12]2)[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 27793801-(Piperidin-4-yl)-1H-benzotriazole--hydrogen chloride (1/1)HCID 53654320alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester

Product 1

HCID 20664159(R)-[(3S,4S)-3-(4-Benzotriazol-1-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-cyclohexyl-acetic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The title compound was prepared from 4-benzotriazol-1-yl-piperidine HCl salt and of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester (prepared above as Aldehyde 5) using procedures analogous to those described in Example 89 Steps C and D except TFA and anisole were used in place of formic acid in Example 89, Step D. ESI-MS 502 (M+1); HPLC A: 2.02 min.

Workup

  1. custom2.02 min.

Sources & evidence

ORD record
ord-c3f925de28c54f7ba739f167d6c4d037
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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