Acetic Anhydride → HCID 69196787, compound

HRID 2219098Notes

Reaction equation

HRID 2219098 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:10]([OH:37])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([CH:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH2:21]2)=[O:19])=[CH:13][CH:12]=1)#[N:9]>N1C=CC=CC=1>[C:8]([C:10]([O:37][C:1](=[O:3])[CH3:2])([C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18]([CH:20]2[O:24][N:23]=[C:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH2:21]2)=[O:19])=[CH:15][CH:16]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)#[N:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18510670HCID 18510670, compound

Product 1

HCID 69196787HCID 69196787, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

) Acetic acid anhydride (0.03 mol) was added dropwise to a solution of (±)-N-[4-(cyanohydroxyphenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (0.010 mol) in pyridine (80 ml), stirred at 0° C. The reaction mixture was stirred for 4 days at RT. The solvent was evaporated. The residue was dissolved in EtOAc and washed with water. The organic layer was separated, dried (Na2SO4), filtered, and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 92/8). The desired fractions were collected and the solvent was evaporated, yielding 2.7 g (61%) of (±)-[cyano-[4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]phenyl]-phenylmethyl]acetate. (compound 83)

Workup

  1. stirringThe reaction mixture was stirred for 4 days at RT
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 92/8)
  10. customThe desired fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-dbc694d12384414d8b6167a286d96de8
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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