Water → HCID 7270102, compound

HRID 736601Notes

Reaction equation

HRID 736601 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@H:19]([CH3:22])[CH2:20][OH:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1.F[B-](F)(F)F.[H+].O>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C@H:19]([CH3:22])[CH2:20][O:21][CH3:1])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 28118Tetrafluoroboric acidHCID 167693Trimethylsilyldiazomethane2×HCID 11779193HCID 11779193, compound

Product 1

HCID 7270102HCID 7270102, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Trimethylsilyl)diazomethane (10 mL, 10 mmol) was added to a vigorously stirred mixture of 4-bromo-N-[(1R)-2-hydroxy-1-methylethyl]benzenesulfonamide (1.0 g, 3.4 mmol) and aqueous fluoroboric acid (conc. 42%, 6.8 mmol) in methylene chloride (25 mL), in 5 portions over 1 h at 0° C. The stirring was continued at 0° C. and another portion of trimethylsilyldiazomethane (5 mL, 5 mmol) was added over 30 min. The stirring was continued for 30 min, poured into water and extracted with methylene chloride. The organic phase was washed with water, dried over sodium sulfate and concentrated. Purification by column chromatography using gradient heptane to heptane/ethylacetate, (2:1), as the eluent gave 0.155 g (15% yield) of the title compound: MS (ESI) 309 m/z (M++1).

Workup

  1. customwas continued at 0° C.
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-b349ad9e4ce749098ebd316720f55b99
Source dataset
uspto-grants-2009_09
Patent number
US07595319B2

Reaction notes

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