Sodium Bicarbonate → HCID 13422902, compound

HRID 2290424Notes

Reaction equation

HRID 2290424 reaction equation
[C:1]1([C:7]2[O:13][C@H]3[C@H:9]([C:10](=[O:14])[NH:11]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O-:18])(O)=O.[Na+]>C(Cl)Cl.CC(C)=CCO>[C:7]([NH:8][C@@H:9]1[C@@H:10]([O:14][CH2:3][CH:2]=[C:1]([CH3:7])[CH3:6])[NH:11][C:15]1=[O:18])(=[O:13])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 13276951HCID 13276951, compound

Product 1

HCID 13422902HCID 13422902, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 111733-Methyl-2-buten-1-OLSolvent

Procedure

181 mg (0.96 mmol--1.2 equivalents) of anhydrous tin-II chloride (dried by fusing briefly under a high vacuum) were added all at once, at 0° C., to a suspension of 150 mg (0.78 mmol) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one in 1.3 ml of anhydrous methlene chloride and 0.81 ml (7.8 mmols--10 equivalents) of 3-methyl-2-buten-1-ol. The cooling bath was removed and a clear solution was formed after a few minutes. The reaction mixture was stirred for a further 15 minutes at room temperature, poured into dilute NaHCO3 solution and extracted with methylene chloride and the extract was washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been filtered on 5 g silica gel (toluene:ethyl acetate 3:7), 153 mg (70%) of the title compound were obtained as colorless crystals, melting point: 92° C., RF : 0.38 (toluene:ethyl acetate 3:7).

Workup

  1. dry with material181 mg (0.96 mmol--1.2 equivalents) of anhydrous tin-II chloride (dried
  2. additionwere added all at once, at 0° C.
  3. customThe cooling bath was removed
  4. customa clear solution was formed after a few minutes
  5. extractionextracted with methylene chloride
  6. washthe extract was washed with water
  7. dry with materialdried over MgSO4
  8. customAfter the solvent had been evaporated off in vacuo
  9. filtrationthe residue had been filtered on 5 g silica gel (toluene:ethyl acetate 3:7)

Sources & evidence

ORD record
ord-049519cc2eb049cda696ba2d2965e2fb
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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