Triethylamine → 1-(2-(3(R)-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(methylsulfonyloxy)propyl)phenyl)ethanone
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH:32]=[CH:33][C:34]2[CH:43]=[CH:42][C:41]3[C:36](=[CH:37][C:38]([Cl:44])=[CH:39][CH:40]=3)[N:35]=2)[CH:27]=1)[OH:25])(=[O:15])[CH3:14].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:44][C:38]1[CH:37]=[C:36]2[C:41]([CH:42]=[CH:43][C:34]([CH:33]=[CH:32][C:28]3[CH:27]=[C:26]([C@H:24]([O:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:23][CH2:22][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:13](=[O:15])[CH3:14])[CH:31]=[CH:30][CH:29]=3)=[N:35]2)=[CH:40][CH:39]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -40 °C
Procedure
At -40° C., methanesulfonyl chloride (1.25 mL, 16.2 mmol) and Et3N (2.8 mL, 20 mmol) were added successively to a solution of the hydroxyketone of Step 4 (6.157 g, 13.44 mmol) in 135 mL of CH2Cl2 and the mixture was stirred at -40° C. for 30 min., then at 0° C. for an hour. A saturated solution of NaHCO3 was added and the title mesylate was extracted into CH2CL2, dried over Na2SO4, concentrated and the remaining traces of water were co-evaporated twice with toluene. This mesylate was used as such in Step 7.
Workup
- waitat 0° C. for an hour
- extractionthe title mesylate was extracted into CH2CL2
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-048dc8e7b6bc4fb08bbb7bc151c81c2f
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212180
Reaction notes
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