Water → HCID 57278229, compound

HRID 893175Notes

Reaction equation

HRID 893175 reaction equation
[CH2:1]([CH:10]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[N:11]1[CH:14]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:17])[CH:13]([CH:28]([OH:30])[CH3:29])[C:12]1=[O:31])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl[C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=1)=[O:43].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:32]([CH:10]([CH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1)[N:11]1[CH:14]([CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:17])[CH:13]([CH:28]([O:30][C:42]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][C:49]([N+:52]([O-:54])=[O:53])=[CH:50][CH:51]=2)=[O:43])[CH3:29])[C:12]1=[O:31])[C:33]1[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 962WaterHCID 782054-Nitrobenzyl chloroformateHCID 57248932HCID 57248932, compound

Product 1

HCID 57278229HCID 57278229, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

2.6 g of 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-p-methoxybenzyloxycarbonylmethyl-2-azetidinone was dissolved in 15 ml of dried methylene chloride, and 1.22 g of 4-dimethylaminopyridine was added thereto. Under ice-cooling, a solution of 1.3 g of p-nitrobenzyl chloroformate in 7 ml of dried methylene chloride was added dropwise to the mixture, followed by stirring at room temperature for 1 hour. To the reaction mixture were added methylene chloride and water, and the methylene chloride layer was washed successively with a 1N hydrochloric acid aqueous solution, water, a 5% aqueous solution of sodium bicarbonate and water, and dried over sodium sulfate. The solvent was removed by distillation, and the residue was purified by silica gel chromatography to obtain 2.2 g of 1-(di-p-anisylmethyl)-3-(1-p-nitrobenzyloxycarbonyloxyethyl)-4-p-methoxybenzyloxycarbonylmethyl-2-azetidinone.

Workup

  1. temperatureUnder ice-cooling
  2. washthe methylene chloride layer was washed successively with a 1N hydrochloric acid aqueous solution, water
  3. dry with materiala 5% aqueous solution of sodium bicarbonate and water, and dried over sodium sulfate
  4. customThe solvent was removed by distillation
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fedf7467a0524e4eb0f6628b1f0e9d40
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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