Acetic Acid → allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464735Notes

Reaction equation

HRID 1464735 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:17](=[O:18])[N:16]2[C@@H:12]1[C@@H:13]([CH3:27])[C:14]([S:25][CH3:26])=[C:15]2[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 57069192allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 80.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) was added to a mixture of 70% aqueous tetrabutylammonium fluoride (0.71 g) and acetic acid (121 mg) in tetrahydrofuran (2 ml) and the mixture was allowed to stand at ambient temperature for 24 hours. The solution was diluted with ethyl acetate (6 ml), washed with water, aqueous sodium bicarbonate solution and brine, and dried. The solvent was removed off under reduced pressure and the residue was crystallized from n-hexane to afford allyl (4R,5S,6S)-6-((1R)-1-hydroxyethyl)-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (58.4 mg).

Workup

  1. washwashed with water, aqueous sodium bicarbonate solution and brine
  2. customdried
  3. customThe solvent was removed off under reduced pressure
  4. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-ad500ece2b014042ad68262e46bb326a
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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