1-[2-(Aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-[2-(3,4-dihydroxybenzoyl)hydrazinyl]-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-[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 1755910Notes

Reaction equation

HRID 1755910 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]([CH2:34][OH:35])[N:33]=[C:29]4[N:28]=[C:27]([C:36](=[O:39])[NH:37][OH:38])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:42][O:43][C:44]([CH3:60])([CH3:59])[C:45]([NH:47][NH:48][C:49](=[O:58])[C:50]1[CH:55]=[CH:54][C:53]([OH:56])=[C:52]([OH:57])[CH:51]=1)=[O:46]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:42]/[O:43][C:44]([C:45](=[O:46])[NH:47][NH:48][C:49](=[O:58])[C:50]2[CH:55]=[CH:54][C:53]([OH:56])=[C:52]([OH:57])[CH:51]=2)([CH3:59])[CH3:60])/[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]([CH2:34][OH:35])[N:33]=[C:29]4[N:28]=[C:27]([C:36](=[O:39])[NH:37][OH:38])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 199179071-[2-(Aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochlorideHCID 86748869(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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 88420350(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-[2-(3,4-dihydroxybenzoyl)hydrazinyl]-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-[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 acidYield 71%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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 (50 mg) (0.082 mmol) and 34 mg (0.11 mmol) of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride are dissolved in 4 ml of absolute dimethylacetamide. After stirring at room temperature for 24 hours the solvent is removed at room temperature. The residue is treated with water. The precipitated product is filtered off under suction and washed in succession with water and diethyl ether. There are obtained 50 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]acetamido]-3-[[[5-(hydroxycarbamoyl)-2-(hydroxymethyl)-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. customis removed at room temperature
  2. additionThe residue is treated with water
  3. filtrationThe precipitated product is filtered off under suction
  4. washwashed in succession with water and diethyl ether

Sources & evidence

ORD record
ord-dfb36c6aee5944f9a918794eb0aaf04e
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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