Methanol → HCID 11139540, compound

HRID 580065Notes

Reaction equation

HRID 580065 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH:16]=CC2C=CC=CC=2)[NH:14][C:13]1=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[OH:26]>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[C@@H:15]([CH2:16][OH:26])[NH:14][C:13]1=[O:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 56606170HCID 56606170, compound

Product 1

HCID 11139540HCID 11139540, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

In a mixture of 80 ml of methanol and 16 ml of dichloromethane is dissolved 0.8 g of (3S,4R)-3-benzyloxycarbonylamino-4-styryl-2-azetidinone obtained in Example 33 and, with cooling at -78° C., ozone gas is bubbled into the solution for 30 minutes. Thereafter, the excess ozone is purged with nitrogen and 0.19 g of sodium borohydride is added, followed by warming the solution to about 0° C. and stirring with ice-cooling for 30 minutes. To the mixture is added 0.3 g of acetic acid and the resulting mixture is concentrated under reduced pressure. To the residue are added ethyl acetate and water, and the ethyl acetate layer is separated. The aqueous layer is extracted with ethyl acetate and the combined ethyl acetate layer is washed with aqueous sodium chloride, dried over mangesium sulfate and concentrated under reduced pressure. The residue is crystallized from diethyl ether and the crystals are collected by filtration to give 0.5 g of (3S,4S)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-azetidinone.

Workup

  1. customozone gas is bubbled into the solution for 30 minutes
  2. customThereafter, the excess ozone is purged with nitrogen and 0.19 g of sodium borohydride
  3. additionis added
  4. temperatureby warming the solution to about 0° C.
  5. temperaturecooling for 30 minutes
  6. additionTo the mixture is added 0.3 g of acetic acid
  7. concentrationthe resulting mixture is concentrated under reduced pressure
  8. additionTo the residue are added ethyl acetate and water
  9. customthe ethyl acetate layer is separated
  10. extractionThe aqueous layer is extracted with ethyl acetate
  11. washthe combined ethyl acetate layer is washed with aqueous sodium chloride
  12. dry with materialdried over mangesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue is crystallized from diethyl ether
  15. filtrationthe crystals are collected by filtration

Sources & evidence

ORD record
ord-ebc948590a244493a7f0da3032292b27
Source dataset
uspto-grants-1988_06
Patent number
US04751299

Reaction notes

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