Acetone → HCID 131713038, compound

HRID 1075222Notes

Reaction equation

HRID 1075222 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([S:15][C:16]([S:18][C@H:19]([CH3:35])[CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[O:23])=[S:17])[NH:13][C:12]1=[O:36])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.[C:38]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][C:47]([N+:50]([O-:52])=[O:51])=[CH:46][CH:45]=1)(=[O:41])[CH:39]=[O:40].CC(C)=O>C1C=CC=CC=1.CCCCCC>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([S:15][C:16]([S:18][C@H:19]([CH3:35])[CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([N+:32]([O-:34])=[O:33])=[CH:30][CH:31]=2)=[O:23])=[S:17])[N:13]([CH:39]([OH:40])[C:38]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][C:47]([N+:50]([O-:52])=[O:51])=[CH:48][CH:49]=2)=[O:41])[C:12]1=[O:36])[CH3:10])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 180AcetoneHCID 21934455p-Nitrobenzyl glyoxylate hydrateHCID 57296186HCID 57296186, compound

Product 1

HCID 131713038HCID 131713038, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8058HexaneSolvent

Procedure

(3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethylthio(thiocarbonyl)]thioazetidin-2-one (10.8 g, 18.8 mmole) and p-nitrobenzyl glyoxylate hydrate (8.53 g, 37.6 mmole) were refluxed in benzene (100 ml) for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was purified by column chromatography (150 g of silica gel), eluted first with a 15% v/v solution of acetone in hexane, giving some unchanged starting compound (1.62 g, 15%), and then with a 30% v/v solution of acetone in hexane, giving the desired compound (12.6 g, 85%) in the form of a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography (150 g of silica gel)
  4. washeluted first with a 15% v/v solution of acetone in hexane
  5. customgiving

Sources & evidence

ORD record
ord-5dd6bf63a6664e21a1efcab89d90c552
Source dataset
uspto-grants-1983_07
Patent number
US04395418

Reaction notes

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