Trifluoroacetic acid → Trifluoroacetic acid

HRID 1096654Notes

Reaction equation

HRID 1096654 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21](=[O:45])[CH2:22][C@H:23]([NH:37]C(=O)OC(C)(C)C)[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH2:35][CH2:34][CH2:33][C:32]3=[O:36])=[CH:27][CH:26]=2)[CH2:16]1.[F:46][C:47]([F:52])([F:51])[C:48]([OH:50])=[O:49]>>[NH2:37][C@@H:23]([CH2:22][C:21]([N:17]1[CH2:18][CH2:19][CH2:20][C@@H:15]([C:7]2[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH2:16]1)=[O:45])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])=[CH:27][CH:26]=1.[C:48]([OH:50])([C:47]([F:52])([F:51])[F:46])=[O:49]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66792397HCID 66792397, compound

Product 2

HCID 6422Trifluoroacetic acidYield 17%HCID 66786233HCID 66786233, compound

Procedure

(tert-Butyl (R)-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxo-1-(4-(2-oxopyrrolidin-1-yl)phenyl)butan-2-ylcarbamate (104A) was dissolved in 25% trifluoroacetic acid and stirred at room temperature for 3 hrs. Solvent was removed under vacuum and the residue was purified by preparatory LC/MS (15-40% CH3CN in H2O) to give the product 1-(4-((R)-2-amino-4-((R)-3-(1-(3-methoxypropyl)-1H-benzo[d]imidazol-2-yl)piperidin-1-yl)-4-oxobutyl)phenyl)pyrrolidin-2-one (209) as a TFA salt (8 mg, 17% yield). ESI-MS:m/z 518.2 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. customthe residue was purified by preparatory LC/MS (15-40% CH3CN in H2O)

Sources & evidence

ORD record
ord-1e6a5e74bf04493a95d94e6c7a9f73bf
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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