Water → (3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1196195Notes

Reaction equation

HRID 1196195 reaction equation
[CH3:1][C:2]([C@H:4]1[N:7]([CH:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:6](=[O:27])[C@@H:5]1[C@H:28]([O:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH3:29])=[CH2:3].[Cl:41]Cl.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C.C(Cl)(Cl)(Cl)Cl>[Cl:41][CH2:3][C:2]([C@H:4]1[N:7]([CH:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:6](=[O:27])[C@@H:5]1[C@H:28]([O:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH3:29])=[CH2:1]

Participants

7

Reactant 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 24526ChlorineHCID 67796403HCID 67796403, compound

Product 1

HCID 67796056(3S,4S)-4-(1-chloromethylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3S,4S)-4-(1-Methylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (200 g) was dissolved in ethyl acetate (3 liters), and a solution of chlorine in carbon tetrachloride (3.85%, 870 g) was added dropwise thereto at room temperature over a period of 15 minutes, followed by stirring for 1 hour. Water (1 liter) and then 10% aqueous sodium thiosulfate (50 ml) were poured into the reaction mixture, which was stirred for 0.5 hour and allowed to stand. The organic layer was washed successively with saturated sodium bicarbonate and brine and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave (3S,4S)-4-(1-chloromethylethenyl)- 3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 84°-85° C.

Workup

  1. stirringwas stirred for 0.5 hour
  2. washThe organic layer was washed successively with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration of the filtrate in vacuo

Sources & evidence

ORD record
ord-30fcb3b668ce4bd1a1eb0d2cb70b48c1
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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