4-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride → 3-[[[5-(Hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755880Notes

Reaction equation

HRID 1755880 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]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([CH3:34])[N:33]=[C:29]4[N:28]=[C:27]([C:35](=[O:38])[NH:36][OH:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=O)N=1.Cl.NOCS(C1C=C(O)C(=CC=1)O)(=O)=O>CC(N(C)C)=O>[OH:37][NH:36][C:35]([C:27]1[CH:26]=[C:25]([S:24][CH2:23][C:15]2[CH2:14][S:13][CH:12]3[N:17]([C:18](=[O:19])[CH2:11]3)[C:16]=2[C:20]([OH:22])=[O:21])[N:30]2[N:31]=[C:32]([CH3:34])[N:33]=[C:29]2[N:28]=1)=[O:38]

Participants

4

Reactant 2

HCID 199179174-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride2×HCID 86748855(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 1317190713-[[[5-(Hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-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-(hydroxycarbamoyl)-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (65 mg) (0.11 mmol) and 37 mg (0.14 mmol) of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol hydrochloride are dissolved in 3 ml of absolute dimethylacetamide. After stirring at room temperature for 24 hours a further 4.2 mg (0.016 mmol) of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol hydrochloride are added. After a further 24 hours the solvent is removed in a high vacuum at room temperature and the residue is treated with water. The precipitated product is filtered off and washed in succession with water and diethyl ether. After drying in a high vacuum there are obtained 55 mg of (6R,7R)-7-[(Z)-2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[[5-(hydroxycarbamoyl)-2-methyl-s-triazolo[1,5 -a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Workup

  1. additionare added
  2. customAfter a further 24 hours the solvent is removed in a high vacuum at room temperature
  3. additionthe residue is treated with water
  4. filtrationThe precipitated product is filtered off
  5. washwashed in succession with water and diethyl ether
  6. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-c9b6e1a4dc844ef787f1b6668025a112
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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