Glycine → HCID 23033862, compound

HRID 1393358Notes

Reaction equation

HRID 1393358 reaction equation
NCC(O)=O.[F:6][C:7]([F:35])([F:34])[C:8]([N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][O:21]C(=O)C(F)(F)F)[C:14]=2[O:13][C:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:11]1)=[O:9].O>CO>[F:35][C:7]([F:6])([F:34])[C:8]([N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][OH:21])[C:14]=2[O:13][C:12]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:11]1)=[O:9]

Participants

5

Reactant 3

HCID 750GlycineHCID 962WaterHCID 23033860HCID 23033860, compound

Product 1

HCID 23033862HCID 23033862, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Glycine buffer (pH 10, 6.33 ml) was added dropwise to a solution of (±)-4-trifluoroacetyl-8-trifluoroacetoxymethyl-2-phenyl-1,4-benzoxazine (953 mg, 2.20 mmol) in methanol (19 ml) at room temperature and the mixture was stirred for 30 min. To the mixture was added water (70 ml) and the mixture was stirred at room temperature for 20 min. and then extracted with ethyl acetate. The extract was washed with water and brine in turn and dried. The solvent was distilled off under reduced pressure to give (±)-4-trifluoroacetyl-2-phenyl-1,4-benzoxazine-8-methanol (793 mg, quantitative yield) as a pale orange oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 min.
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine in turn
  4. customdried
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6f0db4cb8d5e43f8817a008065a55c54
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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