Pyridine → Trans-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2-acetoxyethyl)-2-azetidinone

HRID 867590Notes

Reaction equation

HRID 867590 reaction equation
[NH2:1][CH:2]([C@H:4]1[C@@H:7]([CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[NH:6][C:5]1=[O:14])[CH3:3].N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])=[O:23]>C(Cl)Cl>[N+:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:22]([NH:1][CH:2]([C@H:4]1[C@H:7]([CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[NH:6][C:5]1=[O:14])[CH3:3])=[O:23])([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 11020280o-Nitrobenzyl chloroformateHCID 131715726cis-3-(1-Aminoethyl)-4-(2'-acetoxyethyl)-2-azetidinone

Product 1

HCID 131714341Trans-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2-acetoxyethyl)-2-azetidinoneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trans and cis-3-(1-aminoethyl)-4-(2'-acetoxyethyl)-2-azetidinone (0.6575 g, 0.00328 mole) is dissolved in 10 ml CH2Cl2, cooled to 0° C., and treated with 1.1 mole each of pyridine and o-nitrobenzyl chloroformate. The reaction mixture is stirred at 0° for 20 min, the ice bath is removed and stirring continued for another 30 min. The solution is diluted with CH2Cl2, washed with H2O, dried and evaporated in vacuo. Column chromatography ##STR207## of the residue gives 0.7790 g (0.00206 mole, 63% yield) of the product.

Workup

  1. customthe ice bath is removed
  2. stirringstirring
  3. waitcontinued for another 30 min
  4. additionThe solution is diluted with CH2Cl2
  5. washwashed with H2O
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c7443f7fe5884d05a2744ddda1a38142
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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