Water → Benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate

HRID 1759218Notes

Reaction equation

HRID 1759218 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH:15]=[N:16][CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>O1CCCC1.C(OCC)(=O)C.C(Cl)Cl>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:19](=[O:20])[N:18]2[CH:13]1[S:14][CH2:15][NH:16][CH:17]2[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 962WaterHCID 14230824HCID 14230824, compound

Product 1

HCID 14230825Benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylateYield 87.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
10 °C

Procedure

To a solution of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]oct-3-ene-2-carboxylate (3.0 g.) in tetrahydrofuran (22 ml.) was added alminum amalgam at 4° C., which was prepared by alminium power (1.8 g.) and 0.5% mercuric chloride (4 ml.), and water (0.75 ml.) was added dropwise thereto. After the mixture was stirred at 10° C. for 75 minutes under nitrogen atmosphere, the reaction mixture was diluted with ethyl acetate (50 ml.) and filtered through a pad of Celite. The filter cake was washed with ethyl acetate, and the filtrate and washings were combined, washed twice with an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to leave an oil (2.7 g.). Chromatography on silica gel (15 g.) with a mixed solvent of methylene chloride and ethyl acetate (5:1 by volume) as an eluent gave an amorphous solid (2.64 g.) of benzyl 7-phenoxyacetamido-8-oxo-5-thia-1,3-diazabicyclo[4,2,0]octane-2-carboxylate.

Workup

  1. additionwas added dropwise
  2. filtrationfiltered through a pad of Celite
  3. washThe filter cake was washed with ethyl acetate
  4. washwashed twice with an aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto leave an oil (2.7 g.)

Sources & evidence

ORD record
ord-6e6ee65815954b01bce478be4afe079e
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

Loading…