Acetone → HCID 23346363, compound

HRID 1856362Notes

Reaction equation

[N+:1]([C:4]1[CH:55]=[CH:54][CH:53]=[CH:52][C:5]=1[CH2:6][O:7][C:8]([NH:10][CH:11]1[CH:14]([CH2:15][CH2:16][OH:17])[N:13]([P:18]([CH2:37][C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[N+:48]([O-:50])=[O:49])=[O:39])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]1=[O:51])=[O:9])([O-:3])=[O:2].CC(C)=[O:58].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>C(Cl)Cl>[N+:1]([C:4]1[CH:55]=[CH:54][CH:53]=[CH:52][C:5]=1[CH2:6][O:7][C:8]([NH:10][CH:11]1[CH:14]([CH2:15][C:16]([OH:58])=[O:17])[N:13]([P:18]([CH2:37][C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[N+:48]([O-:50])=[O:49])=[O:39])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]1=[O:51])=[O:9])([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

One gram of 3-(o-nitrobenzyloxycarbonylamino)-1-(o-nitrobenzyloxycarbonylmethyltriphenylphosphoranyl)-4-(2-hydroxyethyl)-2-azetidinone is dissolved in 20 ml. acetone and cooled to 0° C. Jones Reagent (1 ml., 4 N solution) is added dropwise over 5 min. and the resulting solution is stirred at 0° C. for 10 min. Isopropanol (0.1 ml.) is added. The mixture is stirred for another 2 min. The reaction mixture is diluted with CH2Cl2 and filtered. The filtrate is washed with saturated NaCl solutin, dried and evaporated to give the title compound which is used without further purification in the next step.

Workup

stirringThe mixture is stirred for another 2 min
filtrationfiltered
washThe filtrate is washed with saturated NaCl solutin
customdried
customevaporated

Sources & evidence

ORD record: ord-1492c5dafba24878ac4f62d2d2b3b455
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04218459

Reaction notes

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