4-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride → 3-[[[5-(Hydroxycarbamoyl)-2-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

HRID 1755880ノート

反応式

HRID 1755880 の反応式
NC1SC=C(C(=O)C(N[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]([CH3:34])[N:33]=[C:29]4[N:28]=[C:27]([C:35](=[O:38])[NH:36][OH:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=O)N=1.Cl.NOCS(C1C=C(O)C(=CC=1)O)(=O)=O>CC(N(C)C)=O>[OH:37][NH:36][C:35]([C:27]1[CH:26]=[C:25]([S:24][CH2:23][C:15]2[CH2:14][S:13][CH:12]3[N:17]([C:18](=[O:19])[CH2:11]3)[C:16]=2[C:20]([OH:22])=[O:21])[N:30]2[N:31]=[C:32]([CH3:34])[N:33]=[C:29]2[N:28]=1)=[O:38]

参加物

4

反応物 2

HCID 199179174-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride2 回HCID 86748855(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-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

生成物 1

HCID 1317190713-[[[5-(Hydroxycarbamoyl)-2-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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(hydroxycarbamoyl)-2-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 (65 mg) (0.11 mmol) and 37 mg (0.14 mmol) of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol hydrochloride are dissolved in 3 ml of absolute dimethylacetamide. After stirring at room temperature for 24 hours a further 4.2 mg (0.016 mmol) of 4-[[(aminooxy)methyl]sulphonyl]pyrocatechol hydrochloride are added. After a further 24 hours the solvent is removed in a high vacuum at room temperature and the residue is treated with water. The precipitated product is filtered off and washed in succession with water and diethyl ether. After drying in a high vacuum there are obtained 55 mg of (6R,7R)-7-[(Z)-2-amino-4-thiazolyl)-2-[[[(3,4-dihydroxyphenyl)sulphonyl]methoxy]imino]acetamido]-3-[[[5-(hydroxycarbamoyl)-2-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 beige powder.

後処理

  1. additionare added
  2. customAfter a further 24 hours the solvent is removed in a high vacuum at room temperature
  3. additionthe residue is treated with water
  4. filtrationThe precipitated product is filtered off
  5. washwashed in succession with water and diethyl ether
  6. customAfter drying in a high vacuum

出典と根拠

ORDレコード
ord-c9b6e1a4dc844ef787f1b6668025a112
出典データセット
uspto-grants-1995_08
特許番号
US05438052

反応ノート

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