Acetic Acid → HCID 57160014, compound

HRID 1975464Notes

Reaction equation

HRID 1975464 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([C:18]1[CH2:24][C@H:23]2[N:20]([C:21](=[O:35])[C@@H:22]2[C@H:25]([O:27][Si](C(C)(C)C)(C)C)[CH3:26])[C:19]=1[C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[CH2:10][NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[O:6])[CH:2]=[CH2:3].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH:9]([C:18]1[CH2:24][C@H:23]2[N:20]([C:21](=[O:35])[C@@H:22]2[C@H:25]([OH:27])[CH3:26])[C:19]=1[C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[CH2:10][NH:11][C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86747601HCID 86747601, compound

Product 1

HCID 57160014HCID 57160014, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.74 g of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate and 0.54 ml of acetic acid in 9 ml of tetrahydrofuran was added dropwise 3.29 g of 70 % tetrabutylammonium fluoride at room temperature. The mixture was stirred for 20 hours at room temperature. 60 ml of Ethyl acetate and 45 ml of water were added to the reaction mixture and the aqueous layer was extracted three times with ethyl acetate. The extracts were combined, washed in turn with saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was chromatographed on silica gel to give 766 mg of allyl (5R,6S)-3-[2-allyloxycarbonylamino-1-(N-allyloxycarbonylaminomethyl)ethyl]-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate.

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washwashed in turn with saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d8c619f8fc4940068784c29b7286f4b1
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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