Methanol → HCID 68525180, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=2)=[N:12][CH:13]=1)=[O:6].ClC1C=CC=C(C(OO)=[O:39])C=1.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=2)=[O:39])=[N:12][CH:13]=1)=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 3-{4-[5-(3,4-dichlorobenzoylamino)pyridin-2-ylsulfanyl]phenyl}propionate (1.00 g, 2.17 mmol) in dichloromethane (20 mL) was added m-chloroperbenzoic acid (0.620 g, 2.60 mmol) at 0° C. The resulting solution was stirred for 1 hour at 0° C. To the reaction solution was added methanol and stirred for some time. To the resulting solution was then added water, and extracted with dichloromethane. The dichloromethane layer was washed with water, a saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, and evaporated. The obtained residue was recrystallized from ethanol 3 times, to thereby yield 0.790 g of the title compound.
Workup
- stirringstirred for some time
- extractionadded water, and extracted with dichloromethane
- washThe dichloromethane layer was washed with water
- dry with materiala saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate
- customevaporated
- customThe obtained residue was recrystallized from ethanol 3 times
Sources & evidence
- ORD record
- ord-803512b759904d4f854a45f0f4778fa4
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188277B2
Reaction notes
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