Triethylamine → HCID 87870259, compound
Reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=O.[F:8][C:9]([F:35])([F:34])[C:10]1[CH:11]=[C:12]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:13][O:14][CH2:15][C:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([OH:20])[CH2:17][CH2:18][NH2:19].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCCl.CN(C)C1C=CN=CC=1>[F:8][C:9]([F:34])([F:35])[C:10]1[CH:11]=[C:12]([CH:27]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:29]=1)[CH2:13][O:14][CH2:15][C:16]([OH:20])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][CH2:18][NH:19][C:2](=[O:1])[C:4]([F:7])([F:6])[F:5]Participants
Procedure
1-(3,5-bis(trifluoromethyl)benzyloxy)-4-amino-2-phenylbutan-2-ol TFA salt (37 mg, 0.071 mmol) was dissolved in 1,2-dichloroethane (0.6 ml). Triethylamine (0.040 ml, 0.29 mmol) was added to the solution, and followed by addition of trifluoroacetic anhydride (0.013 ml, 0.091 mmol) and catalytic amount of 4-dimethylaminopyridine. After stirred overnight at room temperature, the reaction mixture was concentrated, and the residue was purified by flash chromatography on silica gel to give the desired trifluoroacetamide. 1H NMR (300 MHz, Acetone) δ ppm 8.27 (s, 1 H) 7.95 (s, 2 H) 7.94 (s, 1 H) 7.54–7.61 (m, 2 H) 7.31–7.40 (m, 2 H) 7.23–7.31 (m, 1 H) 4.72–4.84 (m, 2 H) 4.69 (s, 1 H) 3.73–3.84 (m, 2 H) 3.29–3.43 (m, 1 H) 3.19 (ddd, J=19.39, 8.05, 5.86 Hz, 1 H) 2.27 (ddd, J=8.60, 6.40, 4.39 Hz, 2 H); LRMS [ESI, MNa+] m/z calcd for C21H18NO3F9Na 526.10, found 525.97.
Workup
- concentrationthe reaction mixture was concentrated
- customthe residue was purified by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-9f10c1e2c7af42ec946fe01ceb477152
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179926B2
Reaction notes
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