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-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755920Notes

Reaction equation

HRID 1755920 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]=[CH:32][CH:33]=[C:29]4[N:28]=[C:27]([C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=4)[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:44][O:45][C:46]([CH3:62])([CH3:61])[C:47]([NH:49][NH:50][C:51](=[O:60])[C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[C:54]([OH:59])[CH:53]=1)=[O:48]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:44]/[O:45][C:46]([C:47](=[O:48])[NH:49][NH:50][C:51](=[O:60])[C:52]2[CH:57]=[CH:56][C:55]([OH:58])=[C:54]([OH:59])[CH:53]=2)([CH3:61])[CH3:62])/[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]=[CH:32][CH:33]=[C:29]4[N:28]=[C:27]([C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=4)[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 136401246(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[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 136431812(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-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (625 mg) and 500 mg of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride are dissolved in 10 ml of dimethylacetamide and left at room temperature for 24 hours. Thereafter, the solvent is evaporated at 30° C. in a vacuum. The residue is triturated with 30 ml of water, whereby it becomes solid. It is filtered off under suction, washed with water and dried at 0.1 mmHg/40° C. and there are obtained 800 mg of beige (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]-acetamido]-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[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. customThereafter, the solvent is evaporated at 30° C. in a vacuum
  2. customThe residue is triturated with 30 ml of water, whereby it
  3. filtrationIt is filtered off under suction
  4. washwashed with water
  5. customdried at 0.1 mmHg/40° C. and there

Sources & evidence

ORD record
ord-49cb7ff8200048cf9a218fd452462342
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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