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

HRID 1032218Notes

Reaction equation

HRID 1032218 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-hydroxymethyl-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. filtrationwas collected by filtration
  4. washwashed with water
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-7bbb01f70eb24b1e99a7cefe073286b7
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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