Trifluoroacetic acid → HCID 9866556, compound

HRID 1017555Notes

Reaction equation

C([O:5][C:6](=[O:33])[CH2:7][CH:8]([S:17]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)(=[O:19])=[O:18])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:26]([CH:23]1[CH2:24][CH2:25][N:20]([S:17]([CH:8]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][C:6]([OH:33])=[O:5])(=[O:19])=[O:18])[CH2:21][CH2:22]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(4-Benzy-piperidine-1-sulfonyl)-5-phenyl-pentanoic acid tert-butyl ester (1.04 g, 2.2 mmol) was taken up in DCM (5 mL) with stirring and cooled to 0° C. TFA (5 mL) was added slowly and the resulting solution placed in the fridge overnight. Solvents evaporated under reduced pressure to give the title compound as a yellow oil (913 mg, Quant). 1H-NMR δ(MeOD) 7.56-7.11 (10H, m), 3.66-3.56 (3H, m), 2.90-2.59 (6H, m), 2.51 (2H, d, J=6.7 Hz), 2.20 (1H, m), 1.90 (1H, m), 1.62-1.47 (3, m) and 1.25-1.11 (2H, m). 13C-NMR δ(MeOD) 174.5, 142.6, 141.7, 130.6, 130.1, 130.0, 129.7, 127.7, 127.4, 58.7, 47.6, 44.2, 39.2, 35.5, 33.9, 33.7, 33.0. IR Vmax (ATR) 2915, 1709, 1451, 1304, 1133, 1041, 937, 746, 698. ESMS=(M+1) 416.0, (M−1) 414.0.

Workup

customplaced in the fridge overnight
customSolvents evaporated under reduced pressure

Sources & evidence

ORD record: ord-0ae6a2b8a3e4403e8dbd4e579d127725
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479502B1

Reaction notes

Loading…