Trifluoroacetic acid → Trifluoroacetic acid

HRID 1096647Notes

Reaction equation

HRID 1096647 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([NH:37]C(=O)OC(C)(C)C)[CH2:14][C:15]([N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]4[N:27]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:26]5[CH:33]=[CH:34][CH:35]=[CH:36][C:25]=5[N:24]=4)[CH2:18]3)=[O:16])=[CH:8][CH:7]=2)=[CH:2]1.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>>[NH2:37][C@H:13]([CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[CH:11][CH:10]=1)[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]2[N:27]([CH2:28][CH2:29][CH2:30][O:31][CH3:32])[C:26]3[CH:33]=[CH:34][CH:35]=[CH:36][C:25]=3[N:24]=2)[CH2:18]1)=[O:16].[C:47]([OH:49])([C:46]([F:51])([F:50])[F:45])=[O:48]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68098142HCID 68098142, compound

Product 2

HCID 6422Trifluoroacetic acidYield 64%HCID 66785073HCID 66785073, compound

Procedure

tert-Butyl(R)-1-(4-(furan-3-yl)phenyl)-4-((R)-3-(1-(3-methoxypropyl)-1,1-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutan-2-ylcarbamate (54A) was dissolved in 25% trifluoroacetic acid and stirred at room temperature for 3 hrs. Solvent was removed under vacuum and purified by preparatory LC/MS (20-50% CH3CN in H2O) to give product (R)-3-amino-4-(4-(furan-3-yl)phenyl)-1-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)butan-1-one (145) as a TFA salt (32 mg, 64% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (br. s., 1H) 1.72-2.22 (m, 5H) 2.57-3.51 (m, 1H) 3.71 (br. s., 1H) 3.77-4.73 (m, 5H) 6.96 (br. s., 1H) 7.30 (m, 2H) 7.37-7.50 (m, 2H) 7.59 (m, 2H) 7.75 (br. s., 3H) 8.17 (s, 1H). ESI-MS:mlz 501.2 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. custompurified by preparatory LC/MS (20-50% CH3CN in H2O)

Sources & evidence

ORD record
ord-a9c8cb29f43046e0a1ccabaf484e4342
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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