Acetic Acid → HCID 86752087, compound

HRID 862401Notes

Reaction equation

HRID 862401 reaction equation
[Si]([O:8][C@@H:9]([C@H:11]1[C:19](=[O:20])[N:18]2[C@@H:12]1[CH2:13][C:14]([S:34][CH3:35])=[CH:15][CH:16]=[C:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])[CH3:10])(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][C@@H:9]([C@H:11]1[C:19](=[O:20])[N:18]2[C@@H:12]1[CH2:13][C:14]([S:34][CH3:35])=[CH:15][CH:16]=[C:17]2[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([N+:31]([O-:33])=[O:32])=[CH:29][CH:30]=1)=[O:22])[CH3:10]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 86752086HCID 86752086, compound

Product 1

HCID 86752087HCID 86752087, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitrobenzyl (7R,8S)-8-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-5-methylthio-9-oxo-1-azabicyclo [5.2.0]non-2,4-diene-2-carboxylate (213 mg, 0.41 mmol) in anhydride THF (8 ml) was added acetic acid (0.35 ml) and a 1.1M solution in tetrahydrofuran of tetrabutylammonium fluoride (1.9 ml; 2.04 mmol). After stirring for 3 days at ambient temperature, the reaction mixture was diluted with ethyl acetate (20 ml) and then washed with an 5% aqueous solution of NaHCO3 and water. After evaporation of the solvents, the residue was taken up with methylene chloride. The insoluble material was filtered off and identified as 4-nitrobenzyl (7R,8S)-8-[(1R)-1-hydroxyethyl]-5-methylthio-9-oxo-1-azabicyclo[5.2.0]non-2,4-diene-2-carboxylate: The filtrate was concentrated and the residue was purified by chromatography on silica gel eluting with ethyl acetate/dichloromethane 3:7 to give an other batch of the 4-nitrobenzyl (7R,8S)-8-[(1R)-1-hydroxyethyl]-5-methylthio-9-oxo-1-azabicyclo-[5.2.0]non-2,4-diene-2-carboxylate (total=102 mg, 62% overall yield).

Workup

  1. washwashed with an 5% aqueous solution of NaHCO3 and water
  2. customAfter evaporation of the solvents
  3. filtrationThe insoluble material was filtered off
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography on silica gel eluting with ethyl acetate/dichloromethane 3:7

Sources & evidence

ORD record
ord-29368762ed5e42a49812cf233c7f43d2
Source dataset
uspto-grants-1998_02
Patent number
US05719139

Reaction notes

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