2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride → 3-[[[2-[(3,4-Dihydroxybenzenesulphonamido)methyl]-5-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 1755831Notes

Reaction equation

HRID 1755831 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]([CH2:34][NH:35][S:36]([C:39]5[CH:44]=[CH:43][C:42]([OH:45])=[C:41]([OH:46])[CH:40]=5)(=[O:38])=[O:37])[N:33]=[C:29]4[N:28]=[C:27]([CH3:47])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=O)N=1.Cl.NOC(C)(C)C(NO)=O>CC(N(C)C)=O>[OH:46][C:41]1[CH:40]=[C:39]([S:36]([NH:35][CH2:34][C:32]2[N:33]=[C:29]3[N:28]=[C:27]([CH3:47])[CH:26]=[C:25]([S:24][CH2:23][C:15]4[CH2:14][S:13][CH:12]5[N:17]([C:18](=[O:19])[CH2:11]5)[C:16]=4[C:20]([OH:22])=[O:21])[N:30]3[N:31]=2)(=[O:38])=[O:37])[CH:44]=[CH:43][C:42]=1[OH:45]

Participants

4

Reactant 2

HCID 199178372-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochlorideHCID 88419715(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[2-[(3,4-dihydroxybenzenesulphonamido)methyl]-5-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 1317190703-[[[2-[(3,4-Dihydroxybenzenesulphonamido)methyl]-5-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-[[[2-[(3,4-dihydroxybenzenesulphonamido)methyl]-5-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 (0.05 g) and 0.02 g of 2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride are stirred in 0.5 ml of dimethylacetamide for 16 hours at room temperature. The dimethylacetamide is evaporated in a high vacuum, the residue is digested with water and the precipitate formed is filtered off and dried. There is obtained 0.015 g of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[(1-hydroxycarbamoyl)-1-methylethoxy)imino]acetamido]-3-[[[2-[(3,4-dihydroxybenzenesulphonamido)methyl]-5-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 pale beige powder.

Workup

  1. customThe dimethylacetamide is evaporated in a high vacuum
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. customdried

Sources & evidence

ORD record
ord-4e06d1ca27524541b8f51ef34a6d44df
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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