Trifluoroacetic acid → HCID 20664118, compound

HRID 1068195Notes

Reaction equation

HRID 1068195 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][N:21]([C@H:30]([CH:43]5[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]5)[C:31]([O:33]CC5C=CC(OC)=CC=5)=[O:32])[CH2:20]4)[CH2:14][CH2:13]3)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[C:1]1([C:7]2[S:8][C:9]([CH:12]3[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][N:21]([C@H:30]([CH:43]5[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]5)[C:31]([OH:33])=[O:32])[CH2:20]4)[CH2:14][CH2:13]3)=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86757027HCID 86757027, compound

Product 1

HCID 20664118HCID 20664118, compoundYield 104.7%

Procedure

To 28 mg of α-(R)-(3-(S)-((4-(2-phenyl-thiazol-5-yl)-piperidine -1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxybenzyl ester (from Step C) were added 150 mg of anisole and 3 ml of triflouroacetic acid. The reaction was stirred at room temperature for 1 hr. 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 24 mg of the title compound. LC-MS (Method A): Retention Time: 2.72 min. Mass Spectrum: 544 (M+H).

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-48b36c438f214f66942e13f0ec04d694
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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