2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755855Notes

Reaction equation

HRID 1755855 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[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[CH:27][N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:41][O:42][C:43]([CH3:49])([CH3:48])[C:44]([NH:46][OH:47])=[O:45]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:41]/[O:42][C:43]([C:44](=[O:45])[NH:46][OH:47])([CH3:49])[CH3:48])/[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[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[CH:27][N: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 86748847(6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88420354(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-(hydroxyamino)-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 68.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (90 mg) (0.15 mmol) and 34 mg (0.2 mmol) of 2-(aminooxy)-N-hydroxy-2-methylpropionamide hydrochloride are dissolved in 2 ml of absolute dimethylacetamide. After stirring at room temperature for 24 hours the mixture is concentrated in a high vacuum at room temperature and the residue is crystallized from ethanol/diethyl ether. It is filtered off under suction and washed with ether and water. After drying in a high vacuum at room temperature there are obtained 72 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-(hydroxycarbamoyl)-1-methylethoxy]imino]acetamido]-3-[[[5-(3,4-dihydroxyphenyl)-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. customthe residue is crystallized from ethanol/diethyl ether
  3. filtrationIt is filtered off under suction
  4. washwashed with ether and water
  5. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-190234ad65fb460d9762d4e558dcc15a
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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