7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → 7-[[2-[4-(Azidomethyl)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1111750Notes

Reaction equation

HRID 1111750 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](Cl)=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[NH2:15][CH:16]1[C:23](=[O:24])[N:22]2[CH:17]1[S:18][CH2:19][C:20]([CH3:28])=[C:21]2[C:25]([OH:27])=[O:26]>C(OCC)(=O)C>[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:15][CH:16]2[C:23](=[O:24])[N:22]3[CH:17]2[S:18][CH2:19][C:20]([CH3:28])=[C:21]3[C:25]([OH:27])=[O:26])=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 18837-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 20505454p-Azidomethylphenylacetyl chloride

Product 1

HCID 227677437-[[2-[4-(Azidomethyl)phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of p-azidomethylphenylacetyl chloride (0.6 g) and 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (0.6 g) in 250 ml of ethyl acetate was refluxed for 50 minutes after which the solvent was removed under vacuum yielding an oily residue which was purified by chromatography using 60 g of silica gel and benzene-acetone as the eluant to give 7-[[2-[4-(azidomethyl)-phenyl]acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid. M.P. 154°-155° C.

Workup

  1. temperaturewas refluxed for 50 minutes after which the solvent
  2. customwas removed under vacuum
  3. customyielding an oily residue which
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-84f3d5bc63b14211afd8a4bc4bc878e1
Source dataset
uspto-grants-1978_10
Patent number
US04118562

Reaction notes

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