Acetic Acid → HCID 22405587, compound

HRID 441184Notes

Reaction equation

HRID 441184 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.[Si]([O:30][CH:31]([C:63]([F:66])([F:65])[F:64])[CH:32]([NH:36][C:37](=[O:62])[CH2:38][N:39]1[C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:43][CH:42]=[C:41]([NH:51][C:52]([O:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[O:53])[C:40]1=[O:61])[CH:33]([CH3:35])[CH3:34])(C(C)(C)C)(C)C>O1CCCC1>[O:61]=[C:40]1[C:41]([NH:51][C:52]([O:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)=[O:53])=[CH:42][CH:43]=[C:44]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:39]1[CH2:38][C:37]([NH:36][CH:32]([CH:33]([CH3:35])[CH3:34])[CH:31]([OH:30])[C:63]([F:65])([F:64])[F:66])=[O:62]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22405525HCID 22405525, compound

Product 1

HCID 22405587HCID 22405587, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

R=phenoxycarbonyl: Tetra-n-butylammonium fluoride (1.0M in tetrahydrofuran, 0.34 mL) and glacial acetic acid (0.02 mL) were added to dry tetrahydrofuran (1 mL). A solution of N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)-2-(2-oxo-3-phenoxycarbonylamino-6-phenyl-1,2,-dihydro-1-pyridyl)acetamide in dry tetrahydrofuran (2 mL) was added to the reaction vessel, and the addition syringe was washed out with an additional 2 mL tetrahydrofuran. The reaction mixture was stirred for 3 h; diluted with ethyl acetate (50 mL); washed with water and brine; dried and evaporated to an oil which was purified by flash chromatography, eluting with dichloromethane:ethyl acetate (90:10), to afford 2-(2-oxo-3-phenoxycarbonylamino-6-phenyl-1,2-dihydro-1-pyridyl)-N-(3,3,3-trifluoro-2-hydroxy-1-isopropylpropyl)acetamide as a white solid (0.110 g); TLC: Rf =0.30, ethyl acetate:dichloromethane (1:9); MS: m/z=518(M+1).

Workup

  1. washthe addition syringe was washed out with an additional 2 mL tetrahydrofuran
  2. additiondiluted with ethyl acetate (50 mL)
  3. washwashed with water and brine
  4. customdried
  5. customevaporated to an oil which
  6. customwas purified by flash chromatography
  7. washeluting with dichloromethane:ethyl acetate (90:10)

Sources & evidence

ORD record
ord-7e018bd0828d4f5faa23dcd01ca4e577
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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