Trifluoroacetic acid → HCID 3010263, compound

HRID 1068191Notes

Reaction equation

HRID 1068191 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C@@H:20]3[C@@H:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][N:22]([C@H:31]([CH:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)[C:32]([O:34]CC4C=CC(OC)=CC=4)=[O:33])[CH2:21]3)[CH2:15][CH2:14]2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH2:1]([C:8]1[S:12][C:11]([CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C@@H:20]3[C@@H:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][N:22]([C@H:31]([CH:44]4[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]4)[C:32]([OH:34])=[O:33])[CH2:21]3)[CH2:15][CH2:14]2)=[N:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57261222HCID 57261222, compound

Product 1

HCID 3010263HCID 3010263, compoundYield 101.4%

Procedure

To 44 mg of α-(R)-(3-(S)-((4-(5-benzyl-thiazol-2-yl) -piperidine-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester (from Step D) were added 125 mg of anisole and 3 ml of triflouroacetic acid. The reaction was stirred at room temperature for 1 hour. The trifluoroacetic acid was evaporated under reduced pressure. The residue was purified by flash chromatography with 20% MeOH in EtOAc followed by 20% MeOH+2% NH4OH in EtOAc to give 36.7 mg of the title compound. ESI-MS 558 (M+H); HPLC A: 2.59 min.

Workup

  1. customThe trifluoroacetic acid was evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography with 20% MeOH in EtOAc

Sources & evidence

ORD record
ord-0824325ffe554f14a4a3f4dccfbe1780
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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