Methane, dichloromethoxy- → HCID 20140822, compound

HRID 1252201Notes

Reaction equation

HRID 1252201 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][O:9][C:10]([O:12][CH2:13][C:14](O)=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].COC(Cl)[Cl:22]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][O:9][C:10]([O:12][CH2:13][C:14]([Cl:22])=[O:15])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 20140862({[(4-Nitrophenyl)methoxy]carbonyl}oxy)acetic acid

Product 1

HCID 20140822HCID 20140822, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-nitrobenzyloxycarbonyloxyacetic acid (300 mg) and 1,1-dichlorodimethyl ether (1 ml) in ethyl acetate (7.5 ml) was refluxed for 5 hours. The reaction mixture was evaporated to give p-nitrobenzyloxycarbonyloxyacetyl chloride, which was then added to a solution of 2-hydroxymethyl-penem-3-carboxylic acid p-nitrobenzyl ester (168 mg) and triethylamine (0.1 ml) in dichlormethane (10 ml) with ice-cooling, followed by stirring for 1 hour. The reaction mixture was treated by the procedure similar to that described in Example 53 to give 2-p-nitrobenzyloxycarbonyloxyacetoxymethyl-penem-3-carboxylic acid p-nitrobenzyl ester.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-d69eb4a2146948009d3ccfd24a2346f7
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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