2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride → 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[2-(3,4-dihydroxyphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755888Notes

Reaction equation

HRID 1755888 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][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]([C:34]5[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=5)[N:33]=[C:29]4[N:28]=[C:27]([CH3:42])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:45][O:46][C:47]([CH3:53])([CH3:52])[C:48]([NH:50][OH:51])=[O:49]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:45]/[O:46][C:47]([C:48](=[O:49])[NH:50][OH:51])([CH3:53])[CH3:52])/[C:8]([NH:10][CH:11]2[C:18](=[O:19])[N:17]3[CH:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([C:34]5[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=5)[N:33]=[C:29]4[N:28]=[C:27]([CH3:42])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 199178372-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochlorideHCID 136401249(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[2-(3,4-dihydroxyphenyl)-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 1364346377-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[2-(3,4-dihydroxyphenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-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-dihydroxyphenyl)-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 (1.3 g) and 0.44 g of 2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride are dissolved in 10 ml of dimethylacetamide. After standing overnight the mixture is evaporated in a vacuum. The residue is digested with 20 ml of water and the precipitate formed is filtered off under suction and dried. There are obtained 1.15 g of 6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(hydroxycarbamoyl)-1-methylethoxy]imino]acetamido]-3-[[[2-(3,4-dihydroxyphenyl)-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

Workup

  1. customthe mixture is evaporated in a vacuum
  2. customthe precipitate formed
  3. filtrationis filtered off under suction
  4. customdried

Sources & evidence

ORD record
ord-ddb16840412b432aa4e42da766642fd2
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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