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-[[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 1755919Notes

Reaction equation

HRID 1755919 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]([CH3:63])([CH3:62])[C:48]([NH:50][NH:51][C:52](=[O:61])[C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([OH:60])[CH:54]=1)=[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][NH:51][C:52](=[O:61])[C:53]2[CH:58]=[CH:57][C:56]([OH:59])=[C:55]([OH:60])[CH:54]=2)([CH3:62])[CH3:63])/[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

Participants

4

Reactant 2

HCID 199179071-[2-(Aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine 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 136431815(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-[[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 acidYield 93.9%

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 0.79 g of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride are dissolved in 10 ml of dimethylacetamide. After standing overnight the mixture is evaporated in a vacuum. The residue is digested with 25 ml of water and the precipitate formed is filtered off under suction and dried. There are obtained 1.7 g of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-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 as a colourless powder.

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-bb35b74fc49b4de68de630130917ece3
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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