Water → HCID 18510668, compound

HRID 2219099Notes

Reaction equation

HRID 2219099 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-ff182137a93447dd967f3c8037129839
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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