Sulfuric Acid → HCID 59002890, compound

HRID 561174Notes

Reaction equation

HRID 561174 reaction equation
[NH2:1][C:2]1[C:21]2[C:20](=[O:22])[C:19]([C:23]([O:25]CC)=[O:24])=[CH:18][N:7]3[C@@H:8]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([F:28])[C:3]=1[F:29].OS(O)(=O)=O>CC(O)=O.O>[NH2:1][C:2]1[C:21]2[C:20](=[O:22])[C:19]([C:23]([OH:25])=[O:24])=[CH:18][N:7]3[C@@H:8]([CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:9][O:10][C:5]([C:6]=23)=[C:4]([F:28])[C:3]=1[F:29]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 59002851HCID 59002851, compound

Product 1

HCID 59002890HCID 59002890, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of ethyl (3S)-8-amino-9,10-difluoro-2,3-dihydro-7-oxo-3-phenylmethyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate (100 mg, 0.250 mmol) in a mixture of AcOH (0.6 mL) and water (0.5 mL), was added H2SO4 (0.1 mL), the whole mixture was heated under reflux for 3 h. The reaction mixture was poured into ice-water and the resulting precipitates were collected by filtration. The filtered precipitates were suspended in water, filtered, and dried in vacuo to give (3S)-8-amino-9,10-difluoro-2,3-dihydro-7-oxo-3-phenylmethyl-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid (88.0 mg, 95%) as a yellow powder.

Workup

  1. temperaturethe whole mixture was heated
  2. temperatureunder reflux for 3 h
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customThe filtered precipitates
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4e4c04409b0b4a349a302df2d6396fa4
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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