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

HRID 1032212Notes

Reaction equation

HRID 1032212 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([SH:10])[N:7]2[N:11]=[C:12]([CH2:14][OH:15])[N:13]=[C:6]2[N:5]=1)([OH:3])=[O:2].CC(O[CH2:20][C:21]1[CH2:30][S:29][C@@H:24]2[C@H:25]([NH2:28])[C:26](=[O:27])[N:23]2[C:22]=1[C:31]([OH:33])=[O:32])=O.O.N>C(#N)C>[NH2:28][CH:25]1[C:26](=[O:27])[N:23]2[C:22]([C:31]([OH:33])=[O:32])=[C:21]([CH2:20][S:10][C:8]3[N:7]4[N:11]=[C:12]([CH2:14][OH:15])[N:13]=[C:6]4[N:5]=[C:4]([C:1]([OH:3])=[O:2])[CH:9]=3)[CH2:30][S:29][C@H:24]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4413287-Aminocephalosporanic acidHCID 178524652HCID 178524652, compound

Product 1

HCID 1317165467-Amino-3-[(5-carboxy-2-hydroxymethyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acidYield 65.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 130 ml of acetonitrile were suspended 8 g of 5-carboxy-2-hydroxymethyl-7-mercapto-s-triazolo[1,5-a]pyrimidine and 9.53 g of 7-aminocephalosporanic acid and 17 ml of boron trifluoride - ethyl ether complex was added thereto, and the mixture was stirred at room temperature for 5 hours. To the reaction mixture was added 300 ml of water and the mixture was adjusted to pH 2 with conc. aqueous ammonia. Precipitated crystals were collected by filtration, washed with water and with acetone, and dried to obtain 10.1 g of the title compound.

Workup

  1. additionwas added
  2. customPrecipitated crystals
  3. filtrationwere collected by filtration
  4. washwashed with water and with acetone
  5. customdried

Sources & evidence

ORD record
ord-ca76a69eb8644a89b9d7f5c9b92c97b1
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

Loading…