Trifluoroacetic acid → HCID 71737376, compound
Reaction equation
C([O:5][C:6](=[O:39])[CH2:7][C@@H:8]([NH:16][C:17]([C:19]1[N:20]=[C:21]([C:37]#[N:38])[C:22]2[C:27]([C:28]=1[OH:29])=[CH:26][CH:25]=[C:24]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH:23]=2)=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:37]([C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[C:24]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:23]=2)[C:28]([OH:29])=[C:19]([C:17]([NH:16][C@@H:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][C:6]([OH:39])=[O:5])=[O:18])[N:20]=1)#[N:38]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-3-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-4-phenyl-butyric acid tert-butyl ester (50 mg, 0.096 mmol) was dissolved in CH2Cl2 (4 mL) and cooled in an ice bath. Trifluoroacetic acid (4 mL) was added, and the mixture was stirred at r.t. for 2 h. The solvent was evaporated in vacuo, and the residue was partitioned between saturated NaHCO3 and EtOAc. Hydrochloric acid (1 M) was added with vigorous stirring until pH was ˜2. The organic layer was dried over MgSO4 and concentrated. The crude product was first purified by column chromatography (0-40% EtOAc/hexanes+2% AcOH), then by preparative TLC (60% EtOAc/hexanes+2% AcOH) to give 20 mg of the title compound as a pale brown solid. MS: (+) m/z 468.14 (M+1).