Ammonia → 7-Amino-3-[(2,5-bis(hydroxy-methyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid

HRID 1032224Notes

Reaction equation

HRID 1032224 reaction equation
[OH:1][CH2:2][C:3]1[N:14]=[C:6]2[N:7]=[C:8]([CH2:12][OH:13])[CH:9]=[C:10]([SH:11])[N:5]2[N:4]=1.CC(O[CH2:19][C:20]1[CH2:29][S:28][C@@H:23]2[C@H:24]([NH2:27])[C:25](=[O:26])[N:22]2[C:21]=1[C:30]([OH:32])=[O:31])=O.O.N>C(#N)C>[NH2:27][CH:24]1[C:25](=[O:26])[N:22]2[C:21]([C:30]([OH:32])=[O:31])=[C:20]([CH2:19][S:11][C:10]3[N:5]4[N:4]=[C:3]([CH2:2][OH:1])[N:14]=[C:6]4[N:7]=[C:8]([CH2:12][OH:13])[CH:9]=3)[CH2:29][S:28][C@H:23]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4413287-Aminocephalosporanic acidHCID 178519783HCID 178519783, compound

Product 1

HCID 1317165527-Amino-3-[(2,5-bis(hydroxy-methyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acidYield 37.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

In 80 ml of acetonitrile were suspended 7.1 g of 2,5-bis(hydroxymethyl)-7-mercapto-s-triazolo[1,5-a]pyrimidine and 9.1 g of 7-aminocephalosporanic acid, and 15 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, 200 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 5.34 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-9df6d9f6ce924a908b71508baec233ff
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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