Trifluoroacetic acid → HCID 178509553, compound
Reaction equation
C(OC(=O)[NH:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10](=[O:31])[NH:11]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:7][C@H:8]([C:32]1[NH:36][C:35]2[CH:37]=[CH:38][C:39]([C:41]3[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([F:49])[CH:42]=3)=[CH:40][C:34]=2[N:33]=1)[CH2:9][C:10]([NH2:11])=[O:31]Participants
3
Procedure
(S)-tert-butyl(1-(5-(4-cyano-3-fluorophenyl)-1H-benzo[d]imidazol-2-yl)-3-oxo-3-(tritylamino)propyl)carbamate (Preparation 17, 28 mg, 0.042 mmol) was dissolved in trifluoroacetic acid (1.1 mL, 14 mmol) and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, azeotroped with methanol (3×), and purified by silica gel column chromatography eluting with 0-100% CMA80/methylene chloride to afford the title compound (9 mg, 37%) as a white solid.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customazeotroped with methanol (3×)