Trifluoroacetic acid → HCID 10392657, compound

HRID 441178Notes

Reaction equation

HRID 441178 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:43])[N:14]([CH2:29][C:30]([NH:32][CH:33]([CH:40]([CH3:42])[CH3:41])[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])=[O:31])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C(C)(C)C)[CH:19]=2)=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13](=[O:43])[N:14]([CH2:29][C:30]([NH:32][CH:33]([CH:40]([CH3:41])[CH3:42])[C:34](=[O:39])[C:35]([F:38])([F:36])[F:37])=[O:31])[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=2)=[CH:16][CH:17]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 10077327HCID 10077327, compound

Product 1

HCID 10392657HCID 10392657, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[3-benzyloxycarbonylamino-6-(3-tert-butoxyphenyl)-2-oxo-1,2-dihydro-1-pyridyl]-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (78 mg) in dry dichloromethane (3 mL) was added trifluoroacetic acid (57 mg). After 5 h the reaction was incomplete, and additional trifluoroacetic acid (57 mg) was added. After 18 h the reaction mixture was diluted with dichloromethane (50 mL), washed with water and brine, dried, and evaporated to a crude oil which was purified by chromatography, eluting with ethanol:ethyl acetate:dichloromethane (0.5:5:94.5), to give the title compound as a white solid (60 mg); TLC: Rf =0.15, ethanol:ethyl acetate:dichloromethane (0.5:5:94.5); HPLC: tR =6.04, FR=2.0, column A, water:acetonitrile (55:45); MS: m/z=546(M+1).

Workup

  1. washwashed with water and brine
  2. customdried
  3. customevaporated to a crude oil which
  4. customwas purified by chromatography
  5. washeluting with ethanol:ethyl acetate:dichloromethane (0.5:5:94.5)

Sources & evidence

ORD record
ord-8402ad2baa8f47a6ad6248da2dca5658
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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