Water → HCID 18510668, compound

HRID 1370266Notes

Reaction equation

HRID 1370266 reaction equation
[OH:1][CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([CH:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[O:11])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:36]([O:1][CH:2]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]([CH:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13]2)=[O:11])=[CH:7][CH:8]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:38])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18510706HCID 18510706, compound

Product 1

HCID 18510668HCID 18510668, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

) A suspension of compound (50) (0.021 mol), N,N-dimethyl-4-pyridinamine (0.042 mol) and triethylamine (catalytic quantity) in CH2Cl2 (100 ml) was stirred at RT. Acetic acid anhydride (0.042 mol) was added and the resulting reaction mixture was stirred and refluxed until a clear solution was obtained. The mixture was stirred and refluxed for an extra 30 minutes, then cooled to RT. Water was added. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated under reduced pressure, yielding 8.0 g of (±)-[4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]carbonyl]amino]phenyl]phenylmethyl acetate (compound 414).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred
  3. temperaturerefluxed until a clear solution
  4. customwas obtained
  5. stirringThe mixture was stirred
  6. temperaturerefluxed for an extra 30 minutes
  7. temperaturecooled to RT
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be84f748a44841759c6968010a8ded02
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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