Oxygen → 1-Formyl-4-(4-trifluoromethyl-benzenesulfonylamino)-cyclohexanecarboxylic acid ethyl ester
Reaction equation
O=[O+][O-].[CH2:4]([O:6][C:7]([C:9]1(/[CH:29]=C/C)[CH2:14][CH2:13][CH:12]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1)=[O:8])[CH3:5].[O:32]=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH2:4]([O:6][C:7]([C:9]1([CH:29]=[O:32])[CH2:10][CH2:11][CH:12]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH2:13][CH2:14]1)=[O:8])[CH3:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
O3 was passed through a solution of 1-((E)-Propenyl)-4-(4-trifluoromethyl-benzenesulfonylamino)-cyclohexanecarboxylic acid ethyl ester (Intermediate 118, 965 mg, 2.83 mmol) in DCM (30 ml) at −78° C. for 12 min. The solution was kept at −78° C. and O2 gas was passed through it for 10 min. The reaction was monitored by LCMS. When no starting material was present, the reaction mixture was left to warm for 15 mins. The ozonide was then quenched/reduced by adding PS-PPh3 (loading=2.34 mmol/g) (6040 mg, 14.13 mmol) and the solution was left to shake overnight. The reaction was filtered through a fritt and beads and washed with DCM. The DCM filtrate and wash were concentrated in vacuo to yield the title compound as a tan solid (850 mg, 91%). LCMS [M−H]=406.2
Workup
- customwas kept at −78° C.
- waitthe reaction mixture was left
- temperatureto warm for 15 mins
- waitthe solution was left
- filtrationThe reaction was filtered through a fritt and beads
- washwashed with DCM
- washThe DCM filtrate and wash
- concentrationwere concentrated in vacuo
Sources & evidence
- ORD record
- ord-7b88c53f6e2246febfb0c78acc8b1bad
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394858B2
Reaction notes
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