Ethyl Acetate → HCID 70542895, compound

HRID 1447299Notes

Reaction equation

HRID 1447299 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[CH:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12.C(OCC)(=O)C>COC(OC)N(C)C>[CH3:3][N:4]([CH:23]=[N:1][C@@H:2]1[C:23](=[O:24])[N:4]2[CH:5]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[O:11])[C:6]([CH3:9])([CH3:8])[S:7][C@H:3]12)[CH3:5]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 70545261HCID 70545261, compound

Product 1

HCID 70542895HCID 70542895, compoundYield 159.2%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 34 mmoles of p-nitrobenzyl 6-amino-2,2-dimethylpenam-3-carboxylate (6APA p-nitrobenzyl ester) in 100 ml of dimethylformamide dimethylacetal was stirred at room temperature for three hours. The reaction mixture was then poured into a stirred mixture of ice water and ethyl acetate and the organic phase separated. The organic phase was layered over water and the pH adjusted to 1.8 with hydrochloric acid. The acidified aqueous layer was separated, slurried with ethyl acetate, and the pH adjusted to 7.5 with 1 N sodium hydroxide. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated to dryness. The product was obtained as a residual oil and was crystallized in trituration with diethyl ether. There were obtained 11 g (80% yield) of the title compound.

Workup

  1. customthe organic phase separated
  2. customThe acidified aqueous layer was separated
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe product was obtained as a residual oil
  8. customwas crystallized in trituration with diethyl ether

Sources & evidence

ORD record
ord-be4f19f1962448b4a9c8c2bad87ca9e3
Source dataset
uspto-grants-1982_02
Patent number
US04316842

Reaction notes

Loading…