Ethyl Acetate → HCID 21941647, compound

HRID 2216293Notes

Reaction equation

HRID 2216293 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:33]C)=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[CH:7]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl.B(Br)(Br)Br>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:33])=[C:6]([C:8]([CH3:32])([CH3:31])[CH2:9][C:10]([OH:30])([C:26]([F:27])([F:29])[F:28])[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[C:22](=[O:23])[O:21][N:20]=[C:19]([CH3:24])[C:18]=3[CH:25]=2)=[O:12])[CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 10460003HCID 10460003, compound

Product 1

HCID 21941647HCID 21941647, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25134Boron tribromideSolvent

Procedure

43.2 mg of (+)-6-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)valeroylamino]-4-methyl-2,3-benzoxazin-1-one in 2.5 ml of dichloromethane and 0.4 ml of 1 M boron tribromide in dichloromethane are stirred for 1.5 hours at 0° C. and mixed with ethyl acetate and sodium bicarbonate solution. The organic phase is washed with water, dried, concentrated by evaporation, and the residue is chromatographed on silica gel (hexane/ethyl acetate, 1.5+1). After crystallization from diisopropyl ether, 34 mg of (+)-6-[4-(5-bromo-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)valeroylamino]-4-methyl-2,3-benzoxazin-1-one is obtained.

Workup

  1. washThe organic phase is washed with water
  2. customdried
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel (hexane/ethyl acetate, 1.5+1)
  5. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-4d1fbd76c8e24ee68adbc27a29843fdb
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

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