Ethyl Acetate → HCID 20543343, compound

HRID 2286107Notes

Reaction equation

HRID 2286107 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][CH:19]([CH2:25][F:26])[CH2:20][CH2:21][C:22](Cl)=[O:23].[C:27]([O:30][CH2:31]C)(=[O:29])[CH3:28]>>[NH2:18][CH:19]([CH2:25][F:26])[CH2:20][CH2:21][C:22]([NH:13][CH:9]1[C:8](=[O:14])[N:7]2[CH:10]1[S:11][CH2:12][C:5]([CH2:31][O:30][C:27](=[O:29])[CH3:28])=[C:6]2[C:15]([OH:17])=[O:16])=[O:23]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 20254479HCID 20254479, compoundHCID 54152914HCID 54152914, compound

Product 1

HCID 20543343HCID 20543343, 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 4-amino-4-fluoromethylbutyric acid chloride wherein the free amino group is protected with tert-butoxycarbonyl in 50 ml of ethyl acetate is refluxed for two 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-[[4-amino-4-fluoromethylbutyryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. temperatureis refluxed for two 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-5547cb91e6bc4c99b2f3455f9c38778f
Source dataset
uspto-grants-1982_04
Patent number
US04326071

Reaction notes

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