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 1755880노트

반응식

HRID 1755880 반응식
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]

참가 물질

4

반응물 2

HCID 199179174-[[(Aminooxy)-methyl]sulphonyl]pyrocatechol hydrochloride2회HCID 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

생성물 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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-c9b6e1a4dc844ef787f1b6668025a112
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438052

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