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-[(3,4-dihydroxyphenyl)sulfonylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755891Notes

Reaction equation

HRID 1755891 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:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([OH:34])[CH:28]=2)(=[O:26])=[O:25])=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:37][O:38][C:39]([CH3:55])([CH3:54])[C:40]([NH:42][NH:43][C:44](=[O:53])[C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[C:47]([OH:52])[CH:46]=1)=[O:41]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:37]/[O:38][C:39]([C:40](=[O:41])[NH:42][NH:43][C:44](=[O:53])[C:45]2[CH:50]=[CH:49][C:48]([OH:51])=[C:47]([OH:52])[CH:46]=2)([CH3:54])[CH3:55])/[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:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([OH:34])[CH:28]=2)(=[O:26])=[O:25])=[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 86748861(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(3,4-dihydroxyphenyl)sulphonyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88420275(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-[(3,4-dihydroxyphenyl)sulfonylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 84.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(3,4-dihydroxyphenyl)sulphonyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (160 mg) (0.30 mmol) are dissolved in 2.0 ml of dimethylacetamide, treated with 130 mg (0.39 mmol) of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride and stirred at room temperature for 20 hours. The dimethylacetamide is evaporated under a high vacuum and the product is precipitated by the addition of water. The purification is effected by chromatography on silica gel with water/acetonitrile as the eluent. After lyophilization there are obtained 200 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1-[3-(3,4-dihydroxybenzoyl)carbazoyl]-1-methylethoxy]imino]acetamido]-3-[[(3,4-dihydroxyphenyl)sulphonyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white solid.

Workup

  1. customThe dimethylacetamide is evaporated under a high vacuum
  2. customthe product is precipitated by the addition of water
  3. customThe purification

Sources & evidence

ORD record
ord-e4e8ce362a004fb9b81f172a65b60813
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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