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)-1,3,4-oxadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755890Notes

Reaction equation

HRID 1755890 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[O:26][C:27]([C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=4)=[N:28][N:29]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.Cl.[NH2:40][O:41][C:42]([CH3:58])([CH3:57])[C:43]([NH:45][NH:46][C:47](=[O:56])[C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([OH:55])[CH:49]=1)=[O:44]>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:40]/[O:41][C:42]([C:43](=[O:44])[NH:45][NH:46][C:47](=[O:56])[C:48]2[CH:53]=[CH:52][C:51]([OH:54])=[C:50]([OH:55])[CH:49]=2)([CH3:57])[CH3:58])/[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[O:26][C:27]([C:30]4[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([OH:37])[CH:31]=4)=[N:28][N:29]=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 136401251(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 136431799(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)-1,3,4-oxadiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 78.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazol-2-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (80 mg) (0.1 mmol) and 42 mg (0.13 mmol) of 1-[2-(aminooxy)-2-methylpropionyl]-2-(3,4-dihydroxybenzoyl)hydrazine hydrochloride are dissolved in 2 ml of absolute dimethylacetamide. After stirring for 20 hours the mixture is filtered and the mother liquor is concentrated at room temperature in a high vacuum. The residue is crystallized using ethanol/diethyl ether. The product is filtered off and washed with water. After drying in a high vacuum at room temperature there are obtained 65 mg of (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)-1,3,4-oxadiazol-2-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2 -ene-2-carboxylic acid as a yellow powder.

Workup

  1. filtrationis filtered
  2. concentrationthe mother liquor is concentrated at room temperature in a high vacuum
  3. customThe residue is crystallized
  4. filtrationThe product is filtered off
  5. washwashed with water
  6. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-068dfb9b80db465488fe0b57101c8aba
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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