3-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → HCID 21493851, compound

HRID 1730854Notes

Reaction equation

HRID 1730854 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH2:14])[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:2].[Cl:19][CH2:20][C:21]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:22]=1[CH:23]([OH:27])[C:24](Cl)=[O:25]>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:15])[CH:10]2[NH:14][C:24](=[O:25])[CH:23]([C:22]2[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:21]=2[CH2:20][Cl:19])[OH:27])[C:7]=1[C:16]([OH:18])=[O:17])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 137293-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 88807898HCID 88807898, compound

Product 1

HCID 21493851HCID 21493851, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 1.2 g of 2-chloromethyl-4-methoxymandelic acid chloride in 200 ml of ethyl acetate is refluxed for 50 minutes after which the solvent is removed under high vacuum. The resulting product is chromatographed on silica gel using benzene-acetone as the eluant. The product obtained is triturated with ether to give 3-[(acetyloxy)methyl]-7-[[2-[2-(chloromethyl)-4-methoxyphenyl]-2-hydroxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid. M.P. 140°-142° C (dec.).

Workup

  1. temperatureis refluxed for 50 minutes after which the solvent
  2. customis removed under high vacuum
  3. customThe resulting product is chromatographed on silica gel
  4. customThe product obtained
  5. customis triturated with ether

Sources & evidence

ORD record
ord-abfadbee24414cb289b0311d5186f0cf
Source dataset
uspto-grants-1976_11
Patent number
US03994875

Reaction notes

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