Acetic Acid → HCID 15117353, compound

HRID 1029682Notes

Reaction equation

HRID 1029682 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH:11]=[C:10]([C:13]2[CH2:19][C@H:18]3[N:15]([C:16](=[O:30])[C@@H:17]3[C@H:20]([O:22][Si](C(C)(C)C)(C)C)[CH3:21])[C:14]=2[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:8][CH:9]=[C:10]([C:13]2[CH2:19][C@H:18]3[N:15]([C:16](=[O:30])[C@@H:17]3[C@H:20]([OH:22])[CH3:21])[C:14]=2[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH2:11][CH2:12]1)=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 15117351HCID 15117351, compound

Product 1

HCID 15117353HCID 15117353, compoundYield 38.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.94 g) in tetrahydrofuran (38 ml) were added dropwise acetic acid (1.65 ml) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1M, 9.6 ml) at 0° C. After standing at ambient temperature for 8 hours, the reaction mixture was taken up into a mixture of ethyl acetate (300 ml) and water (300 ml). After adjusting pH to around 7 with aqueous sodium hydrogen carbonate the organic layer was separated washed in turn with water and brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (25 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V) to give allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (281 mg).

Workup

  1. customat 0° C
  2. customwas separated
  3. washwashed in turn with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas chromatographed on silica gel (25 g)
  8. washeluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V)

Sources & evidence

ORD record
ord-204618079d31443f93695a6dae0fbed9
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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