Dimethyl Sulfoxide → HCID 86603599, compound

HRID 271997Notes

Reaction equation

HRID 271997 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH2:29][CH2:30][OH:31])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][CH2:18]2)=[O:16])[C:12]([Cl:32])=[CH:11][C:10]=1[F:33])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([C:15]([N:17]2[CH2:22][CH2:21][C:20]([CH2:29][CH:30]=[O:31])([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][CH2:18]2)=[O:16])[C:12]([Cl:32])=[CH:11][C:10]=1[F:33])(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 69183040HCID 69183040, compound

Product 1

HCID 86603599HCID 86603599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of N-(tert-butyl)-4-chloro-2-fluoro-5-{[6-(2-hydroxyethyl)-6-phenyl-1,3-oxazinan-3-yl]carbonyl}benzenesulfonamide (25.2 mg, 0.05 mmol) in dimethyl sulfoxide (71 μL, 1 mmol), diisopropylethylamine (53 μL, 0.30 mmol) and 1 mL CH2Cl2 was added SO3.pyr in one portion. The reaction mixture was stirred for 2 h at 0° C., saturated aqueous NaHCO3 was added, and the aqueous layer was extracted with CHCl3. After evaporation, the resultant crude N-(tert-butyl)-4-chloro-2-fluoro-5-{[6-(2-oxoethyl)-6-phenyl-1,3-oxazinan-3-yl]carbonyl}benzenesulfonamide was obtained and used in the next step without further purification.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3
  2. customAfter evaporation

Sources & evidence

ORD record
ord-ff1b029008f94d11b657aff1b6c88599
Source dataset
uspto-grants-2008_11
Patent number
US07452992B2

Reaction notes

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