Ethyl Acetate → HCID 22405461, compound

HRID 441215Notes

Reaction equation

HRID 441215 reaction equation
FC(F)(F)[C:3]([N:5]([C:7]1[C:8](=[O:33])[N:9]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)C)=O.C(OCC)(=O)C>[Cl-].[Na+].O>[CH3:3][NH:5][C:7]1[C:8](=[O:33])[N:9]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:31])[CH3:32])[C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])=[O:21])[C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 22405488HCID 22405488, compound

Product 1

HCID 22405461HCID 22405461, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Using a procedure similar to that described above under Example 49.j. for the basic hydrolysis of the analogous 3-(N-trifluoroacetylamino) compound to the 3-amino-compound, but using the following extractive work-up, the title compound was prepared from 2-[3-(N-trifluoroacetyl-N-methylamino)-2-oxo-6-phenyl -1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl -2-oxopropyl)acetamide. On completion of hydrolysis, ethyl acetate and brine were added. The organic phase was separated, washed (brine), dried (MgSO4), and evaporated. The resultant solid was triturated with diethyl ether, chromatographed, eluting with dichloromethane:methanol (96:4), and dried overnight under vacuum to give the title product as a white solid; TLC: Rf =0.20, dichloromethane:methanol (96:4); MS: m/z=410(M+1).

Workup

  1. additionwere added
  2. customThe organic phase was separated
  3. washwashed (brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe resultant solid was triturated with diethyl ether
  7. customchromatographed
  8. washeluting with dichloromethane:methanol (96:4)
  9. customdried overnight under vacuum

Sources & evidence

ORD record
ord-a829f94132434107b3f6fdcc7153695e
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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