Water → (3S,4S)-4-(1-(R)-carboxyethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

HRID 21720

Reaction equation

HRID 21720 reaction equation
[OH:1][CH2:2][C@@H:3]([C@@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])[CH3:4].CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[C:2]([C@@H:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH3:11])[CH3:4])([OH:25])=[O:1]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 13960427(3S,4S)-4-(1-(R)-hydroxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinoneHCID 131709961Jones' reagent

Product 1

HCID 13960430(3S,4S)-4-(1-(R)-carboxyethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

A solution of (3S,4S)-4-(1-(R)-hydroxymethylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (6.1 g) in acetone (60 ml) was treated with the Jones reagent, prepared from chromium trioxide (2.78 g), 98% sulfuric acid (4.4 g) and water (8.1 ml), at 10°-20° C. for 1 hour. The reaction mixture was quenched with isopropanol (0.5 ml) at 10°-20° C. for 15 minutes, diluted with ethyl acetate (122 ml) and washed with water (135 ml). The aqueous layer was separated from the organic layer and extracted with ethyl acetate (61 ml). The ethyl acetate extracts and the organic layer were combined together and extracted with 5% aqueous sodium bicarbonate solution (30 ml). The extract was washed with dichloromethane (60 ml) and acidified with 10% hydrochloric acid solution (20 ml) with ice-cooling. The acidic solution was extracted twice with dichloromethane (60 ml). The extracts were washed with brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo to give (3S,4S)-4-(1-(R)-carboxyethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. customThe reaction mixture was quenched with isopropanol (0.5 ml) at 10°-20° C. for 15 minutes
  2. additiondiluted with ethyl acetate (122 ml)
  3. washwashed with water (135 ml)
  4. customThe aqueous layer was separated from the organic layer
  5. extractionextracted with ethyl acetate (61 ml)
  6. extractionextracted with 5% aqueous sodium bicarbonate solution (30 ml)
  7. washThe extract was washed with dichloromethane (60 ml)
  8. temperaturecooling
  9. extractionThe acidic solution was extracted twice with dichloromethane (60 ml)
  10. washThe extracts were washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationAfter filtration
  13. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b76297b7782a4dedb693a126d3a0daab
Source dataset
uspto-grants-1995_06
Patent number
US05424422

Linked notes

Loading…