ethyl (3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate → (3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid

HRID 561177Notes

Reaction equation

HRID 561177 reaction equation
[NH2:1][C:2]1[C:16]2[C:15](=[O:17])[C:14]([C:18]([O:20]CC)=[O:19])=[CH:13][N:7]3[C@@H:8]([CH2:11][F:12])[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([F:23])[C:3]=1[F:24]>OS(O)(=O)=O.O.CC(O)=O>[NH2:1][C:2]1[C:16]2[C:15](=[O:17])[C:14]([C:18]([OH:20])=[O:19])=[CH:13][N:7]3[C@@H:8]([CH2:11][F:12])[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([F:23])[C:3]=1[F:24]

Participants

3

Reactant 1

HCID 59002916ethyl (3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate

Product 1

HCID 66999235(3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 86597087Acetic acid sulfuric acid waterSolvent

Procedure

A suspension of ethyl (3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (270 mg, 0.789 mmol) in a mixture of H2SO4—H2O—AcOH (1:5:6, 3 mL) was heated under reflux for 1 h. The reaction mixture was poured into ice-water and the resulting precipitates were collected by filtration. The filtered precipitates were washed with water, and dried in vacuo to give (3R)-8-amino-9,10-difluoro-3-fluoromethyl-2,3-dihydro-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (237 mg, 96%) as a yellow powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 h
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customThe filtered precipitates
  6. washwere washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9ebeb553f5c849638d8635bb5d4265e2
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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