Water → HCID 59532363, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][C:18]([CH2:27][CH2:28][OH:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:17][C:16]2=[O:30])[CH:10]=1.CCN(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40].O>C(Cl)Cl>[CH3:38][S:39]([O:29][CH2:28][CH2:27][C:18]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:17][C:16](=[O:30])[N:15]([C:11]2[CH:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[CH:14]=[CH:13][CH:12]=2)[CH2:20][CH2:19]1)(=[O:41])=[O:40]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(2′,4′-difluorobiphenyl-3-yl)-6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-2-one (200 mg, 0.49 mmol) in dry CH2Cl2 (4 mL) was added Et3N (0.234 mL, 1.46 mmol) at 0˜5° C. A solution of methanesulfonyl chloride (67 mg, 0.59 mmol) in dry CH2Cl2 (1 mL) was added dropwise at the same temperature. After addition, the mixture was allowed to warm to it gradually. When the reaction was complete, water (10 mL) was added and the mixture was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with 10% aq citric acid, satd aq NaHCO3 and brine, then dried over Na2SO4, filtered and concentrated to give 2-(3-(2′,4′-difluorobiphenyl-3-yl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl methanesulfonate (230 mg, 97%), which was used in the next step without purification.
Workup
- additionAfter addition
- temperatureto warm to it gradually
- extractionthe mixture was extracted with CH2Cl2 (3×10 mL)
- washThe combined organic layers were washed with 10% aq citric acid
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6f243d32beef49428e733e9bcc421301
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575156B2
Reaction notes
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