Water → HCID 10208636, compound

HRID 1836193Notes

Reaction equation

HRID 1836193 reaction equation
[Br:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]([CH3:34])([CH3:33])[CH2:11][C:12]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[C:24](=[O:25])[O:23][N:22]=[C:21]([CH3:26])[C:20]=2[CH:27]=1)=[O:14].B(Br)(Br)Br.O>ClCCl>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]([CH3:34])([CH3:33])[CH2:11][C:12]([OH:32])([C:28]([F:29])([F:30])[F:31])[C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]2[C:24](=[O:25])[O:23][N:22]=[C:21]([CH3:26])[C:20]=2[CH:27]=1)=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 21908315HCID 21908315, compound

Product 1

HCID 10208636HCID 10208636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

78 mg of (+)-6-[4-(2-bromo-3-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeroylamino]-4-methyl-2,3-benzoxazin-1-one is mixed in 1.4 ml of dichloromethane at 0° C. with 0.71 ml of a 1 molar solution of boron tribromide in dichloromethane. After 2 hours of stirring at 0° C., the mixture is added to water, extracted with ethyl acetate, the organic phase is dried (Na2SO4) and concentrated by evaporation. After the residue is triturated with hexane, the title compound is obtained in crystalline form, flash point 226-231° C., [α]D=+91.1° (c=0.5 in chloroform)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. customAfter the residue is triturated with hexane

Sources & evidence

ORD record
ord-14c78aae52bb4f619ef3e5a9d1d49b2f
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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