Methanesulfonyl chloride → {3,4-Dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate
Reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.CCOCC>[CH3:32][S:33]([O:20][CH2:19][C:17]1[CH:18]=[C:13]([CH2:12][N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:11])[C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=1)(=[O:35])=[O:34]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1,1-dimethylethyl cyclopropyl{[2,3-dichloro-5-(hydroxymethyl)phenyl]methyl}carbamate (1 eq.) from the previous step in dichloromethane (0.1 M) was added sequentially at 0 Hunig's base (3 eq.) and methanesulfonyl chloride (1.1 eq.). The resulting solution was stirred at 0° C. for 30 min and then at RT for 15 min. The reaction mixture was then diluted with ether and carefully quenched with 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a colorless oil.
Workup
- waitat RT for 15 min
- customcarefully quenched with 1 N aq. HCl
- customThe aqueous layer was separated
- extractionback-extracted with ether
- washThe combined organic extracts were washed further with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-d7101ec58c7d4660b1084fe09efc01e5
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889714B2
Reaction notes
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