Dichloromethane → HCID 22855052, compound

HRID 1755918Notes

Reaction equation

HRID 1755918 reaction equation
B(F)(F)F.CCOCC.CC(O[CH2:14][C:15]1[CH2:24][S:23][C@@H:18]2[C@H:19]([NH2:22])[C:20](=[O:21])[N:17]2[C:16]=1[C:25]([OH:27])=[O:26])=O.[OH:28][NH:29][C:30](=[O:44])[CH2:31][CH2:32][C:33]1(S)[CH:38]=[CH:37][N:36]2[NH:39][C:40]([CH3:42])=[N:41][C:35]2=[N:34]1.ClCCl.ClCCl.[S:51]1(CCCC1)(=O)=O>>[NH2:22][C@@H:19]1[C:20](=[O:21])[N:17]2[C@@H:18]1[S:23][CH2:24][C:15]([CH2:14][S:51][C:37]1[N:36]3[N:39]=[C:40]([CH3:42])[N:41]=[C:35]3[N:34]=[C:33]([CH2:32][CH2:31][C:30](=[O:44])[NH:29][OH:28])[CH:38]=1)=[C:16]2[C:25]([OH:27])=[O:26]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8000Boron trifluoride etherateHCID 4413287-Aminocephalosporanic acidHCID 69712587Dichloromethane sulpholaneHCID 178432411HCID 178432411, compound

Product 1

HCID 22855052HCID 22855052, compound

Procedure

Boron trifluoride diethyl etherate (2 ml) are added dropwise at 0° C. to a suspension of 305 mg (1.12 mmol) of 7-aminocephalosporanic acid and 318 mg (1.25 mmol of N-hydroxy-5-mercapto-2-methyl-s-triazolo[1,5-a]pyrimidine-5-propionamide in 4 ml of dichloromethane/sulpholane (1:1 v/v). Subsequently, the mixture is stirred at room temperature for 16 hours. The solution is treated with 50 ml of dichloromethane. A beige substance crystallizes out. It is filtered off, washed with diethyl ether and dissolved in 5 ml of water. The solution is adjusted to about pH 4 with aqueous sodium hydrogen carbonate solution. The product is crystallized by the addition of about 100 ml of ethanol. The crystals are filtered off, washed with ethanol and dried at room temperature in a high vacuum. There are obtained 311 mg of (6R,7R)-7-amino-3-[[[5-[2-(hydroxycarbamoyl)ethyl]-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.

Workup

  1. customA beige substance crystallizes out
  2. filtrationIt is filtered off
  3. washwashed with diethyl ether
  4. dissolutiondissolved in 5 ml of water
  5. customThe product is crystallized by the addition of about 100 ml of ethanol
  6. filtrationThe crystals are filtered off
  7. washwashed with ethanol
  8. customdried at room temperature in a high vacuum

Sources & evidence

ORD record
ord-fe2bd192c5ad4c32809fcf24e12c0859
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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