O-[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methyl]hydroxylamine hydrochloride → 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755845Notes

Reaction equation

HRID 1755845 reaction equation
NC1SC=C(C(=O)C(N[C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15](CSC2C(C4C=CC(O)=C(O)C=4)=CN=C(C4C=CC=CC=4)N=2)=[C:16]3[C:20]([OH:22])=[O:21])=O)N=1.Cl.FC1C2OC(C3C=CC=CC=3)(C3C=CC=CC=3)OC=2C=CC=1CON>CC(N(C)C)=O>[O:19]=[C:18]1[N:17]2[CH:12]([S:13][CH2:14][CH:15]=[C:16]2[C:20]([OH:22])=[O:21])[CH2:11]1

Participants

4

Reactant 2

HCID 19918004O-[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methyl]hydroxylamine hydrochlorideHCID 86748843(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 190919938-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (66 mg) (0.1 mmol) and 47 mg (0.13 mmol) of O-[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methyl]hydroxylamine hydrochloride are dissolved in 1 ml of absolute of dimethylacetamide. After stirring at room temperature for 20 hours the mixture is concentrated in a high vacuum at room temperature and the residue is treated with 0.45 ml of ethanol and 3 ml of water. The precipitated product is filtered off and washed with water. After drying in a high vacuum at room temperature there are obtained 98 mg of (6R,7R)-7-[(Z)-2(2-amino-4-thiazolyl)-2-[[(4-fluoro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]imino]acetamido]-3-[[5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Workup

  1. concentrationis concentrated in a high vacuum at room temperature
  2. additionthe residue is treated with 0.45 ml of ethanol and 3 ml of water
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water
  5. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-ed75d384aa3f48aa90cff08aa7f726b3
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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