Bistrimethylsilylacetamid → 7beta-[2-(Tetrazol-1-yl)-acetylamino]-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid

HRID 127649Notes

Reaction equation

HRID 127649 reaction equation
C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[NH2:13][C@@H:14]1[C:31](=[O:32])[N:16]2[C:17]([C:28]([OH:30])=[O:29])=[C:18]([S:21][C:22]3[N:26]([CH3:27])[N:25]=[N:24][N:23]=3)[CH2:19][S:20][C@H:15]12.[N:33]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[N:36][N:35]=[N:34]1>C(Cl)Cl>[N:33]1([CH2:38][C:39]([NH:13][C@@H:14]2[C:31](=[O:32])[N:16]3[C:17]([C:28]([OH:30])=[O:29])=[C:18]([S:21][C:22]4[N:26]([CH3:27])[N:25]=[N:24][N:23]=4)[CH2:19][S:20][C@H:15]23)=[O:40])[CH:37]=[N:36][N:35]=[N:34]1

Participants

5

Reactant 3

HCID 11708267BistrimethylsilylacetamidHCID 13232854(1H-Tetrazol-1-yl)acetyl chlorideHCID 705626647beta-Amino-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid

Product 1

HCID 705644447beta-[2-(Tetrazol-1-yl)-acetylamino]-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.306 ml (1.27 mmols) of bis-trimethylsilylacetamide is added to a suspension of 200 mg (0.63 mmol) of 7β-amino-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid in 3.2 ml of methylene chloride and the mixture is stirred under nitrogen at room temperature for 40 minutes. The solution is cooled to 0° C., 224 mg (1.52 mmols) of tetrazol-1-ylacetyl chloride are added and the mixture is stirred for 11/2 hours at 0° C. and extracted with aqueous sodium bicarbonate solution. The pH of the aqueous phase is adjusted to 1.5 and this phase is extracted with ethyl acetate. The organic phase is dried over sodium sulphate and evaporated in a rotary evaporator and gives 7β-[2-(tetrazol-1-yl)-acetylamino]-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid; thin layer chromatogram (silica gel; butanol/acetic acid/water, 75:7.5:21), Rf value 0.17; IR spectrum (nujol); characteristic bands at 3400, 1780, 1720 and 1690 cm-1.

Workup

  1. temperatureThe solution is cooled to 0° C.
  2. stirringthe mixture is stirred for 11/2 hours at 0° C.
  3. extractionextracted with aqueous sodium bicarbonate solution
  4. extractionthis phase is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-875adfaf210744f8a85fd700ab53a1a3
Source dataset
uspto-grants-1981_03
Patent number
US04256739

Reaction notes

Loading…