Water → HCID 57550278, compound

HRID 1642209Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(4-Trifluoromethyl-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (HVB01043, 0.2 g, 0.43 mmol) was dissolved in anhydrous DCM (5 ml), cooled to 0° C. and to this was added TFA (2.3 ml), and the reaction mixture was stirred under nitrogen for 1 h. The reaction mixture was poured onto solid potassium carbonate (6 g), and water (25 ml) added. Extracted with DCM and the organic layers dried over anhydrous magnesium sulphate, and evaporated in-vacuo, to afford an off white oil, 0.14 g, 89%. Rf: 0.47 (DCM), 1HNMR: (CDCl3, 270 MHz) δ 1.65 (2H, m, CHCH2), 1.79 (2H, m, CHCH2), 2.30 (1H, m, CH), 2.64 (2H, td, J=12.4, 2.7 Hz, NCH2), 3.10 (2H, m, NCH2), 6.97 (1H, dd, J=6.4, 30.5 Hz, Ar HD), 7.05 (2H, m, Ar HF), 7.06 (1H, m, Ar HB), 7.17 (1 h, t, J=7.2 Hz, Ar HC), 7.58, d, J=8.6 Hz, Ar HE), 8.39 (1H, d, J=7.9 Hz, Ar HA).

Workup

additionadded
extractionExtracted with DCM
dry with materialthe organic layers dried over anhydrous magnesium sulphate
customevaporated in-vacuo
customto afford an off white oil, 0.14 g, 89%

Sources & evidence

ORD record: ord-a2d173967356457aa8286c1f5f5e34d6
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119627B2

Reaction notes

Loading…