Ethyl Acetate → (6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

HRID 2231605Notes

Reaction equation

HRID 2231605 reaction equation
[CH3:1][C:2]1([CH3:14])[O:9][CH2:8][CH2:7][CH:6]2[N:3]1[C:4](=[O:13])[CH:5]2[N:10]=[N+]=[N-].[C:15]([O:18][CH2:19][CH3:20])(=[O:17])C>[Pd]>[CH3:1][C:2]1([CH3:14])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:13])[C@@H:5]2[NH:10][C:15]([O:18][CH2:19][C:20]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:17]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 12769232HCID 12769232, compound

Product 1

HCID 13744719(6R,7R)-7-benzyloxycarbonylamino-2,2-dimethyl-1-aza-3-oxabicyclo[4.2.0]octan-8-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In 20 ml of ethyl acetate is dissolved 940 mg of 2,2-dimethyl-7-azido-1-aza-3-oxabicyclo[4,2,0]octan-8-one (1:4 cis-trans mixture) and catalytic reduction is carried out using 300 mg of 10% palladium-on-carbon (wet). The catalyst is then filtered off and washed with ethyl acetate. The filtrate and washings are combined and concentrated to about 20 ml. Then, 4 ml of propylene oxide and 0.9 ml of carbobenzoxy chloride are added and the mixture is stirred at room temperature for 1.5 hours and concentrated. The residue is subjected to column chromatography using silica gel (60 g), elution being carried out with chloroform-ethyl acetate (6:4) to give 388 mg of cis-(2,2-dimethyl-7-benzyloxyformamido-1-aza-3-oxabicyclo[4,2,0]octan-8-one) as the first product.

Workup

  1. filtrationThe catalyst is then filtered off
  2. washwashed with ethyl acetate
  3. concentrationconcentrated to about 20 ml
  4. additionThen, 4 ml of propylene oxide and 0.9 ml of carbobenzoxy chloride are added
  5. concentrationconcentrated
  6. washsilica gel (60 g), elution

Sources & evidence

ORD record
ord-6aa20815e8354299b7cd143238b1804c
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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