Hydrochloric Acid → 7-Amino-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid

HRID 1395772Notes

Reaction equation

HRID 1395772 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:14][C:13]([SH:15])=[N:12][N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].CC(O[CH2:25][C:26]1[CH2:35][S:34][C@@H:29]2[C@H:30]([NH2:33])[C:31](=[O:32])[N:28]2[C:27]=1[C:36]([OH:38])=[O:37])=O.Cl>CC(C)=O>[NH2:33][CH:30]1[C:31](=[O:32])[N:28]2[C:27]([C:36]([OH:38])=[O:37])=[C:26]([CH2:25][S:15][C:13]3[S:14][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[N:11][N:12]=3)[CH2:35][S:34][C@H:29]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178453124HCID 178453124, compound

Product 1

HCID 142074127-Amino-3-(5-t-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acidYield 56.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Tert-butoxycarbonylaminomethyl-1,3,4-thiadiazole-2-thiol (1.24 g.) was dissolved in acetone (10 ml.). The solution was added to the aqueous solution (40 ml.) containing sodium bicarbonate (0.84 g.). The mixed solution was warmed on water bath heating at 70°-75° C. To the solution was added all at once 7-aminocephalosporanic acid (1.35 g.) at 55° C. The mixture was stirred at 65°-70° C. for 2 hrs. and then cooled to 0°-5° C. with ice. The reaction mixture was adjusted to pH 5.0-5.2 with 10% hydrochloric acid. The precipitating pale yellow substance was separated out by filtration, washed with water and acetone, and then dried to give 7-amino-3-(5-tert-butoxycarbonylaminomethyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (1.28 g.). m.p. over than 220° C.

Workup

  1. additionThe solution was added to the aqueous solution (40 ml.)
  2. temperatureThe mixed solution was warmed on water bath
  3. temperatureheating at 70°-75° C
  4. temperatureand then cooled to 0°-5° C. with ice
  5. customThe precipitating pale yellow substance was separated out by filtration
  6. washwashed with water and acetone
  7. customdried

Sources & evidence

ORD record
ord-8acee22d982e4cbc8362d5145309fa0b
Source dataset
uspto-grants-1980_05
Patent number
US04205166

Reaction notes

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