Ethyl Acetate → HCID 20254447, compound

HRID 1903841Notes

Reaction equation

HRID 1903841 reaction equation
C(O[C:5]1[CH2:12][S:11][CH:10]2[N:7]([C:8](=[O:14])[CH:9]2[NH2:13])[C:6]=1[C:15]([OH:17])=[O:16])(=O)C.[NH2:18][C:19]([CH:27]([F:29])[F:28])([CH2:23][CH2:24][CH2:25][NH2:26])[C:20](Cl)=[O:21].[CH2:30]([O:32][C:33](=[O:35])[CH3:34])C>>[NH2:18][C:19]([CH:27]([F:29])[F:28])([CH2:23][CH2:24][CH2:25][NH2:26])[C:20]([NH:13][CH:9]1[C:8](=[O:14])[N:7]2[CH:10]1[S:11][CH2:12][C:5]([CH2:30][O:32][C:33](=[O:35])[CH3:34])=[C:6]2[C:15]([OH:17])=[O:16])=[O:21]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 20254479HCID 20254479, compoundHCID 53855542HCID 53855542, compound

Product 1

HCID 20254447HCID 20254447, compound

Procedure

A mixture of 1 g of 3-acetyloxy-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and 1 g of 2,5-diamino-2-difluoromethylvaleric acid chloride wherein the free amino groups are protected with tert-butoxycarbonyl in 50 ml of ethylacetate is refluxed for 2 hours after which the solvent is removed leaving a residue which is treated with mild acid and chromatographed on silica gel using benzene-acetone as the eluant to give 7-[[2,5-diamino-2-difluoromethylvaleryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. temperatureis refluxed for 2 hours after which the solvent
  2. customis removed
  3. customleaving a residue which
  4. additionis treated with mild acid
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-74d0821336264d8494ab38ac033f3d52
Source dataset
uspto-grants-1984_03
Patent number
US04438270

Reaction notes

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