Acetic Acid → HCID 57741110, compound
Reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][CH:20]=3)[CH:12]=2)[C@@H:9]([O:27][C:28](=[O:30])[CH3:29])[C@H:8]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[C@@H:6]1[O:40][C:41](=[O:43])[CH3:42])(=[O:3])[CH3:2].C(O)(=[O:46])C>O>[C:1]([O:4][C@H:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25](=[O:46])[CH3:26])=[CH:23][CH:24]=3)[CH:12]=2)[C@@H:9]([O:27][C:28](=[O:30])[CH3:29])[C@H:8]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[C@@H:7]([O:36][C:37](=[O:39])[CH3:38])[C@@H:6]1[O:40][C:41](=[O:43])[CH3:42])(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 125 °C
Procedure
To a vigorously stirred solution of (1S,2R,3R,4S,5R,6R)-4-(acetoxymethyl)-6-(4-chloro-3-(4-ethylbenzyl)phenyl)cyclohexane-1,2,3,5-tetrayl tetraacetate (19) (300 mg, 48.7 μmol) in acetic acid (5 mL) was added K2Cr2O7 (172 mg, 0.58 mmol) and the mixture was stirred for 22 hours at 125° C. The mixture was cooled to room temperature, diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with saturated NaHCO3 (3×10 mL) and then with brine (20 mL), dried (Na2SO4), filtered and concentrated. Preparative TLC (2:1 hexane:ethyl acetate) afforded 100 mg of the desired compound. MS (ESI+): 631 [M+H]+, 648 [M+H2O]+.
Workup
- temperatureThe mixture was cooled to room temperature
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic extracts were washed with saturated NaHCO3 (3×10 mL)
- dry with materialwith brine (20 mL), dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fa672bb41c304c48b7812dc5ae3e6b74
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129434B2
Reaction notes
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