Ammonia → 7-Amino-3-[(5-hydroxymethyl2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid

HRID 1032589Notes

Reaction equation

HRID 1032589 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([SH:9])[N:6]2[N:10]=[C:11]([CH3:13])[N:12]=[C:5]2[N:4]=1.CC(O[CH2:18][C:19]1[CH2:28][S:27][C@@H:22]2[C@H:23]([NH2:26])[C:24](=[O:25])[N:21]2[C:20]=1[C:29]([OH:31])=[O:30])=O.O.N>C(#N)C>[NH2:26][CH:23]1[C:24](=[O:25])[N:21]2[C:20]([C:29]([OH:31])=[O:30])=[C:19]([CH2:18][S:9][C:7]3[N:6]4[N:10]=[C:11]([CH3:13])[N:12]=[C:5]4[N:4]=[C:3]([CH2:2][OH:1])[CH:8]=3)[CH2:28][S:27][C@H:22]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4413287-Aminocephalosporanic acidHCID 178432392HCID 178432392, compound

Product 1

HCID 1317165487-Amino-3-[(5-hydroxymethyl2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acidYield 56.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

In 120 ml of acetonitrile were suspended 9.8 g of 5-hydr- oxymethyl-7-mercapto-2-methyl-s-triazolo[1,5-a]pyrimidine and 13.6 g of 7-aminocephalosporanic acid, and 22 ml of boron trifluoride-ethyl ether complex was added to the suspension and the mixture was stirred at 50° C. for 3 hours. After cooling the reaction mixture, 250 ml of water was added thereto and the mixture was adjusted to pH 2 with conc. aqueous ammonia. Precipitated crystal was collected by filtration, washed with water, washed with acetone and then dried to obtain 11.6 g of the title compound.

Workup

  1. additionwas added to the suspension
  2. additionwas added
  3. customPrecipitated crystal
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-039cddc1782f475d87525b8d84f1a6bc
Source dataset
uspto-grants-1990_09
Patent number
US04958019

Reaction notes

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