Water → trans 1-(o-Nitrobenzyloxycarbonylhydroxymethyl)-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2'-acetoxyethyl)-2-azetidinone

HRID 867591Notes

Reaction equation

HRID 867591 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])(=[O:4])[CH:2]=[O:3].O.[N+:17]([C:20]1[CH:43]=[CH:42][CH:41]=[CH:40][C:21]=1[CH2:22][O:23][C:24]([NH:26][CH:27]([C@H:29]1[C@H:32]([CH2:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])[NH:31][C:30]1=[O:39])[CH3:28])=[O:25])([O-:19])=[O:18]>C1C=CC=CC=1>[N+:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][O:5][C:1]([CH:2]([OH:3])[N:31]1[C@@H:32]([CH2:33][CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@H:29]([CH:27]([NH:26][C:24]([O:23][CH2:22][C:21]2[CH:40]=[CH:41][CH:42]=[CH:43][C:20]=2[N+:17]([O-:19])=[O:18])=[O:25])[CH3:28])[C:30]1=[O:39])=[O:4])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 12833475(2-Nitrophenyl)methyl oxoacetateHCID 131714341Trans-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2-acetoxyethyl)-2-azetidinone

Product 1

HCID 131714340trans 1-(o-Nitrobenzyloxycarbonylhydroxymethyl)-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2'-acetoxyethyl)-2-azetidinoneYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ortho-nitrobenzyl glyoxalate preferred from (0.650 g, 0.00153 mole) of di-o-nitrobenzyl tartarate, is dissolved in 20 ml benzene and refluxed using a Dean-Stark water separator containing CaH2 for an hour. Trans-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2-acetoxyethyl)-2-azetidinone (0.580 g, 0.00153 mole) is added and the mixture is refluxed for 8 hrs, cooled, evaporated. The residue is column chromatographed ##STR210## to give 0.775 g (0.00132 mole, 87% yield) of the product.

Workup

  1. temperaturerefluxed
  2. additionseparator containing CaH2 for an hour
  3. temperaturethe mixture is refluxed for 8 hrs
  4. temperaturecooled
  5. customevaporated
  6. customchromatographed ##STR210##

Sources & evidence

ORD record
ord-191b8fd2eb9e4ad2b3e4cef253d3f0b2
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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