Water → HCID 67796345, compound

HRID 1196196Notes

Reaction equation

HRID 1196196 reaction equation
Cl[CH2:2][C:3]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4].O.C1(C)C=CC(S(O)(=O)=[O:50])=CC=1.P(=O)(O)(O)O>CS(C)=O.C(OCC)(=O)C>[OH:50][CH2:2][C:3]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])=[CH2:4]

Participants

7

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 6101p-Toluenesulfonic acidHCID 67796056(3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Product 1

HCID 67796345HCID 67796345, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (20 g) in dimethylsulfoxide (160 ml) were successively added water (40 ml), cuprous oxide (6.76 g) and p-toluenesulfonic acid (7.6 g), and the resultant mixture was warmed to 50° to 55° C. and stirred for 2 hours at the same temperature. After cooling down to room temperature, 1% aqueous phosphoric acid (90 ml) and ethyl acetate (200 ml) were poured into the reaction mixture, followed by stirring for 0.5 hour. An insoluble material was removed by filtration over celite and washed 3 times with ethyl acetate (20 ml). The filtrate and the washings were combined together, and the aqueous layer was separated from the organic layer and extracted with ethyl acetate (200 ml). The organic layer and the extract were combined together, washed with brine and dried over anhydrous sodium sulfate. After filtration and concentration of the filtrate in vacuo, the concentrate was crystallized from a mixture of toluene and n-hexane (1:1) to give crystals of (3S,4S)-4-(1-hydroxymethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)- 1-di(p-anisyl)methyl-2-azetidinone. m.p., 118°-120° C.

Workup

  1. stirringby stirring for 0.5 hour
  2. customAn insoluble material was removed by filtration over celite
  3. washwashed 3 times with ethyl acetate (20 ml)
  4. customthe aqueous layer was separated from the organic layer
  5. extractionextracted with ethyl acetate (200 ml)
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration and concentration of the filtrate in vacuo
  9. customthe concentrate was crystallized from a mixture of toluene and n-hexane (1:1)

Sources & evidence

ORD record
ord-3f91f69c4d6641489076ce6c4de7d6da
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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