Acetic Acid → allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1029686Notes

Reaction equation

HRID 1029686 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:29])[C@@H:16]3[C@H:19]([O:21][Si](C(C)(C)C)(C)C)[CH3:20])[C:13]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[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[CH2:11][CH2:10][CH:9]([C:12]2[CH2:18][C@H:17]3[N:14]([C:15](=[O:29])[C@@H:16]3[C@H:19]([OH:21])[CH3:20])[C:13]=2[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 15117359allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 15117368allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 41.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-t-butyldimethylsilyoxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.9 g) in tetrahydrofuran (30 ml) were added acetic acid (3.3 ml) and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (28.7 ml) at 0° C. under nitrogen. After standing at ambient temperature for 7 hours and additionally at 5° C. for 14 hours, the reaction mixture was taken up into a mixture of ethyl acetate and water. After adjusting pH to around 7 with an aqueous sodium hydrogen carbonate, the organic layer was separated, washed in turn with water and brine, and dried over magnesium sulfate. Removal of the solvent gave a residue, which was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:2, V/V) to give allyl (5R,6S)-3-(1-allyloxycarbonylpyrrolidin-3-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.94 g).

Workup

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

Sources & evidence

ORD record
ord-470fe7be5ac948b688e5183c71ff632c
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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