Water → HCID 178519778, compound

HRID 1943688Notes

Reaction equation

HRID 1943688 reaction equation
C([O:8][C:9]1[CH:13]=[C:12]([C:14]([N:16]2[CH2:21][CH2:20][O:19][C:18]3[CH:22]=[CH:23][N:24]=[CH:25][C:17]2=3)=[O:15])[O:11][N:10]=1)C1C=CC=CC=1.O.C(=O)([O-])O.[Na+]>Br.C(O)(=O)C>[O:19]1[CH2:20][CH2:21][N:16]([C:14]([C:12]2[O:11][N:10]=[C:9]([OH:8])[CH:13]=2)=[O:15])[C:17]2[CH:25]=[N:24][CH:23]=[CH:22][C:18]1=2

Participants

6

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 66936639HCID 66936639, compound

Product 1

HCID 178519778HCID 178519778, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

In 3 ml of 33% hydrobromic acid in acetic acid solution, (3-benzyloxy -isoxazol-5-yl)-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-methanone (45 mg, 0.13 mmol) was dissolved and then stirred at room temperature for 24 hours. After completion of the reaction by adding water dropwise, the mixture was adjusted to weak acidic condition (pH=6) by using saturated solution of sodium hydrogen carbonate and extracted with ethyl acetate. The aqueous layer was evaporated under reduced pressure and the residue was purified by using preparative TLC plate to obtain the target compound 44, i.e., (2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-yl)-(3-hydroxy-isoxazol-5-yl)-methanone, as white solid (8 mg, 24%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. customThe aqueous layer was evaporated under reduced pressure
  4. customthe residue was purified

Sources & evidence

ORD record
ord-2de8ee52154f48b4a8ad3de5a6866b2c
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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