2-Methyl-2-butene → HCID 67777705, compound

HRID 1026267Notes

Reaction equation

HRID 1026267 reaction equation
[F:1][C:2]1[C:3]([O:9][CH2:10][C@@H:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])=[N:4][O:5][C:6]=1[CH:7]=[O:8].P([O-])(O)(O)=[O:22].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>O.CC(O)(C)C>[C:16]([O:15][C:14]([NH:13][C@@H:11]([CH3:12])[CH2:10][O:9][C:3]1[C:2]([F:1])=[C:6]([C:7]([OH:22])=[O:8])[O:5][N:4]=1)=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86666286HCID 86666286, compound

Product 1

HCID 67777705HCID 67777705, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

To a mixture of tert-butyl {(1S)-2-[(4-fluoro-5-formylisoxazol-3-yl)oxy]-1-methylethyl}carbamate (244 mg), sodium dihydrogen phosphate (305 mg), 2-methylbut-2-ene (449 mL), 2-methylpropan-2-ol (5 mL) and water (1 mL) was added sodium chlorite (115 mg) at room temperature, and the obtained mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with a mixed solvent of ethyl acetate/2-propanol (volume ratio 3/1). The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a white powder (256 mg).

Workup

  1. extractionthe mixture was extracted with a mixed solvent of ethyl acetate/2-propanol (volume ratio 3/1)
  2. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-039fa24e783842c3973a3cce68ebe287
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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