3-((Acetyloxy)methyl)-7-amino-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid → HCID 21493865, compound

HRID 1730855Notes

Reaction equation

HRID 1730855 reaction equation
[Cl:1][CH2:2][C:3]1[S:7][C:6]([CH2:8][C:9](Cl)=[O:10])=[CH:5][CH:4]=1.[C:12]([O:15][CH2:16][C:17]1[CH2:24][S:23][CH:22]2[N:19]([C:20](=[O:26])[CH:21]2[NH2:25])[C:18]=1[C:27]([OH:29])=[O:28])(=[O:14])[CH3:13]>C(OCC)(=O)C>[C:12]([O:15][CH2:16][C:17]1[CH2:24][S:23][CH:22]2[N:19]([C:20](=[O:26])[CH:21]2[NH:25][C:9](=[O:10])[CH2:8][C:6]2[S:7][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=2)[C:18]=1[C:27]([OH:29])=[O:28])(=[O:14])[CH3:13]

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 227677535-Chloromethyl-2-thienylacetyl chloride

Product 1

HCID 21493865HCID 21493865, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.2 equivalents of 5-chloromethyl-2-thienylacetyl chloride and 1 equivalent of 3-[(acetyloxy)-methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is refluxed for 50 minutes in ethyl acetate after which the solvent is removed and the remaining product is purified by column chromatography on silica gel to give 3-[(acetyloxy)methyl]-7-[[2-[5-(chloromethyl)-2-thienyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. customis removed
  2. customthe remaining product is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e377d1e51efd4e079b01ad793f037b04
Source dataset
uspto-grants-1976_11
Patent number
US03994875

Reaction notes

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