7-Aminocephalosporanic acid → 7-Amino-3-(1-carbamoylmethyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid

HRID 2049562Notes

Reaction equation

HRID 2049562 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[N:24]([CH2:25][C:26]([NH2:28])=[O:27])[N:23]=[N:22][N:21]=1.C(=O)(O)[O-].[Na+]>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[N:24]([CH2:25][C:26](=[O:27])[NH2:28])[N:23]=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 3

HCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178514025HCID 178514025, compound

Product 1

HCID 128510887-Amino-3-(1-carbamoylmethyl-1H-tetrazol-5-ylthio)methylceph-3-em-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

7-Aminocephalosporanic acid (5.44 g., 20 mmole) and 5-Mercapto-1H-tetrazol-1-ylacetamide (3.50 g., 2.2 mmole) were suspended in 50% aqueous acetone (200 ml) and solid sodium bicarbonate added until a clear solution was obtained, ~pH 7.0. The solution was heated at 60° for 6 hours, uncovered for the final hour which allowed most of the acetone to evaporate, then acidified to pH 4.0 and stirred in an ice bath for one hour. The solid product was collected, washed with a little cold water and dried in vacuo, 3.22 g (43.4%), δ(CF3CO2H) 4.00 (2H,bs, C2 methylene), 4.69 (2H,bs, --CH2S--), 5.56 (4H,s, --CH2CO2NH2 and β-lactam protons), 7.4-7.8 (2H,m, --CONH2).

Workup

  1. customwas obtained
  2. temperatureThe solution was heated at 60° for 6 hours
  3. customto evaporate
  4. customThe solid product was collected
  5. washwashed with a little cold water
  6. dry with materialdried in vacuo, 3.22 g (43.4%), δ(CF3CO2H) 4.00 (2H,bs, C2 methylene), 4.69 (2H,bs, --CH2S--), 5.56 (4H,s, --CH2CO2NH2 and β-lactam protons), 7.4-7.8 (2H,m, --CONH2)

Sources & evidence

ORD record
ord-37f47bd91b9447bd9439ccd940ebe67d
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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