Methyl propionate → HCID 14356366, compound

HRID 622587Notes

Reaction equation

HRID 622587 reaction equation
N([C@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9][C:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N+]=[N-].C(OC)(=O)CC>C1(C)C=CC=CC=1>[C:10]([NH:9][CH:5]1[CH2:4][NH:7][C:6]1=[O:8])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11124Methyl propionateHCID 53771027HCID 53771027, compound

Product 1

HCID 14356366HCID 14356366, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.0 g of (3S,4R)-4-azido-3-tritylamino-2-azetidinone in 35 ml of toluene is added 1.14 g of methyl propionate and the mixture is refluxed for 2 hours. The solvent is then distilled off under reduced pressure and the residue is purified by silica gel column chromatography using n-hexane-ethyl acetate (2:1). The earlier eluate fractions are combined and concentrated under reduced pressure to give 0.818 g of (3S,4R)-[5-methoxycarbonyl)-1,2,3-triazol-1-yl]-3-tritylamino-2-azetidinone (compound A).

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. distillationThe solvent is then distilled off under reduced pressure
  3. customthe residue is purified by silica gel column chromatography
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-95305e5fe2f04188942a3e67fc6d4e98
Source dataset
uspto-grants-1988_09
Patent number
US04771045

Reaction notes

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