Methanesulfonic Acid → HCID 88420175, compound

HRID 1755868Notes

Reaction equation

HRID 1755868 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](=[O:37])[NH:35][OH:36])[N:33]=[C:29]4[N:28]=[C:27]([CH3:38])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[NH2:40][O:41][CH2:42][C:43]1[N:48]([CH3:49])[C:47](=[O:50])[C:46]([OH:51])=[CH:45][N:44]=1.CS(O)(=O)=O>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:40]/[O:41][CH2:42][C:43]2[N:48]([CH3:49])[C:47](=[O:50])[C:46]([OH:51])=[CH:45][N:44]=2)/[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](=[O:37])[NH:35][OH:36])[N:33]=[C:29]4[N:28]=[C:27]([CH3:38])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 19917929HCID 19917929, compoundHCID 86748850HCID 86748850, compound

Product 1

HCID 88420175HCID 88420175, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[2-(hydroxycarbamoyl)-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 (65 mg) (0.11 mmol) are dissolved in 4 ml of absolute dimethylacetamide. 24 mg (0.14 mmol) of 2-[(aminooxy)methyl]-5-hydroxy-3-methyl-4(3H)-pyrimidinone and 14 mg (0.14 mmol) of methanesulphonic acid are added. After stirring at room temperature for 20 hours the dimethylacetamide is evaporated in a high vacuum and the residue is taken up in water and stirred for 15 minutes in order to precipitate the product completely. The product is filtered off, washed with water and diethyl ether and dried in a high vacuum at room temperature. There are obtained 48 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(1,6-dihydro-5-hydroxy-1-methyl-6-oxo-2-pyrimidinyl)methoxy]imino]acetamido]-3-[ [[2-(hydroxycarbamoyl)-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 beige powder.

Workup

  1. customis evaporated in a high vacuum
  2. customto precipitate the product completely
  3. filtrationThe product is filtered off
  4. washwashed with water and diethyl ether
  5. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-b75e03f1f0d943eb8630a48999a9299e
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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