Hydrochloric Acid → HCID 70582401, compound

HRID 2049566Notes

Reaction equation

HRID 2049566 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[O:24][C:23]([C:25]([NH2:27])=[O:26])=[N:22][N:21]=1.C(=O)(O)[O-].[Na+].Cl>CC(C)=O>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[O:24][C:23]([C:25](=[O:26])[NH2:27])=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178513838HCID 178513838, compound

Product 1

HCID 70582401HCID 70582401, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-Aminocephalosporanic acid (10.88 g, 40 mmole) and 5-mercapto-1,3,4-oxadiazol-2-ylcarboxamide (6.40 g, 44 mmole) in 50% aqueous acetone (500 ml) were treated with solid sodium bicarbonate to pH 7 then heated at 60° for 5 hours. The solution was acidified to pH 4.0 with 5 N hydrochloric acid, cooled in an ice bath for one hour and the precipitated solid collected, washed with water (100 ml) ethanol (200 ml) and ether (200 ml) and dried in vacuo, 5.87 g (41.1%), δ(CF3CO2H) 3.5-4.1 (2H,m, C2 methylene), 4.4-4.9 (2H,m, --CH2S--), 5.42 (2H,s, β-lactam protons), 7.89 (2H, d, J 28 Hz, --CONH2).

Workup

  1. temperaturethen heated at 60° for 5 hours
  2. temperaturecooled in an ice bath for one hour
  3. customthe precipitated solid collected
  4. washwashed with water (100 ml) ethanol (200 ml) and ether (200 ml)
  5. dry with materialdried in vacuo, 5.87 g (41.1%), δ(CF3CO2H) 3.5-4.1 (2H,m, C2 methylene), 4.4-4.9 (2H,m, --CH2S--), 5.42 (2H,s, β-lactam protons), 7.89 (2H, d, J 28 Hz, --CONH2)

Sources & evidence

ORD record
ord-40feb39cb8f44a74abf9ea3bcbcff8d4
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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