Trifluoroacetic acid → HCID 86602087, compound
Reaction equation
[CH2:1]([NH-:5])[CH2:2][CH2:3][CH3:4].[CH2-]C(C)=[O:8].[CH:10]12[CH2:18][CH:14]([C:15]1([CH3:17])[CH3:16])C[CH2:12][CH:11]2C.F[C:21](F)(F)[C:22]([OH:24])=O>>[CH2:1]([NH-:5])[CH2:2][CH2:3][CH3:4].[C:14]12([OH:8])[CH2:18][CH:10]([C:15]1([CH3:17])[CH3:16])[CH2:11][CH2:12][C:22]2([OH:24])[CH3:21]Participants
Procedure
Pinane acetonide butylamide 8 (107 mg, 0.35 mmol) was stirred with a 1:1 mixture of trifluoroacetic acid (TFA)/water (3 ml) at room temperature. The reaction was monitored by TLC and showed about 75% conversion to the cis-diol after 2 hours, then the reaction stalled and the intensity of a new spot between starting material and product started to build up. The unknown byproduct may be formed from fragmentation of the pinane ring in product 9 under the acidic condition. The optimal reaction time was about 3.5 hours. The reaction mixture was neutralized with saturated NaHCO3 solution, and then was extracted 3 times with 50% EtOAc/hex. The combined organic extract was washed with H2O, dried over anhydrous Na2SO4 and concentrated. Residual unreacted starting material 8 and byproduct from the pinanediol butylamide 9 was not removed by silica chromatography. IR (CHCl3): 3455, 3390, 3000, 2960, 2930, 2875, 1647, 1530, 1463, 1385, 1140, 1117, 1054, 1033 and 1018 cm−1.
Workup
- customafter 2 hours
Sources & evidence
- ORD record
- ord-7e6989165dfa4aa69be4bbadc79ab914
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399645B2
Reaction notes
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