Trifluoroacetic acid → HCID 57968603, compound
Reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C@H:9]1[C:20]([N:22]1[CH2:28][CH2:27][CH2:26][N:25]([CH:29]2[CH2:32][CH2:31][CH2:30]2)[CH2:24][CH2:23]1)=[O:21])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([C@H:11]1[CH2:12][NH:8][C@H:9]([C:20]([N:22]2[CH2:28][CH2:27][CH2:26][N:25]([CH:29]3[CH2:32][CH2:31][CH2:30]3)[CH2:24][CH2:23]2)=[O:21])[CH2:10]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (2S,4R)-4-benzyl-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (350.8 mg, 0.794 mmol) in CH2Cl2 (2 mL) was treated with TFA (0.5 mL). After 16 h, the mixture was concentrated and the residue was purified by FCC(CH2Cl2 to 10% MeOH/0.1% NH4OH in CH2Cl2) to give the title compound (266.3 mg, 98%). MS (ESI): mass calcd. for C21H31N3O, 341.25; m/z found, 342.3 [M+H]+. 1H NMR (CDCl3): 7.35-7.29 (m, 2H), 7.28-7.22 (m, 1H), 7.16 (d, J=7.9 Hz, 2H), 4.91-4.80 (m, 1H), 4.03-3.38 (m, 4H), 3.20-2.90 (m, 2H), 2.85-2.33 (m, 7H), 2.25-1.56 (m, 11H).