Ethyl Acetate → 7-[[2-Amino-4-carboxy-2-vinylbutyryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 26033Notes

Reaction equation

HRID 26033 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.C([O:25][C:26]([CH:28](C(Cl)=O)[CH2:29][C@@:30]([CH:35]=[CH2:36])([C:32](Cl)=[O:33])[NH2:31])=[O:27])C1C=CC=CC=1.[C:40]([O:43][CH2:44]C)(=[O:42])[CH3:41]>>[NH2:31][C:30]([CH:35]=[CH2:36])([CH2:29][CH2:28][C:26]([OH:25])=[O:27])[C:32]([NH:13][CH:9]1[C:8](=[O:14])[N:7]2[CH:10]1[S:11][CH2:12][C:5]([CH2:44][O:43][C:40](=[O:42])[CH3:41])=[C:6]2[C:15]([OH:17])=[O:16])=[O:33]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 20254479HCID 20254479, compoundHCID 1317114684-Benzyloxycarbonyl-2-vinylglutamic acid chloride

Product 1

HCID 213264337-[[2-Amino-4-carboxy-2-vinylbutyryl]amino]-3-acetyloxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Procedure

A mixture of 1 gram 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-benzyloxycarbonyl-2-vinylglutamic acid chloride wherein the free amino group is protected with tert-butoxycarbonyl in 50 ml of ethyl acetate 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-amino-4-carboxy-2-vinylbutyryl]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-2026099d10f34ea6944e179b7fb3fa7e
Source dataset
uspto-grants-1979_04
Patent number
US04147873

Reaction notes

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