Ethyl chloroformate → HCID 178475890, compound

HRID 851692Notes

Reaction equation

HRID 851692 reaction equation
[C:1]([O:5][C:6]([N:8]=[C:9]1[NH:13][C:12]([C:14](=[O:18])[C:15]([OH:17])=O)=[CH:11][S:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C.[CH3:25][C:26]([O:28][CH2:29][C:30]1[CH2:39][S:38][C@@H:33]2[C@H:34]([NH2:37])[C:35](=[O:36])[N:32]2[C:31]=1[C:40]([OH:42])=[O:41])=[O:27]>C(Cl)Cl.CN(C)CCCO.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]=[C:9]1[NH:13][C:12]([C:14](=[O:18])[C:15]([NH:37][CH:34]2[C:35](=[O:36])[N:32]3[C:31]([C:40]([OH:42])=[O:41])=[C:30]([CH2:29][O:28][C:26](=[O:27])[CH3:25])[CH2:39][S:38][C@H:33]23)=[O:17])=[CH:11][S:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 10928Ethyl chloroformateHCID 4413287-Aminocephalosporanic acidHCID 178453003HCID 178453003, compound

Product 1

HCID 178475890HCID 178475890, compound

Reagents, catalysts & solvents 3

HCID 766463-(Dimethylamino)-1-propanolCatalystHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent2×

Procedure

2.7 g of 2-(2-tert.-butoxycarbonylimino-4-thiazolin-4-yl)-glyoxylic acid containing one molar equivalent of crystal alcohol are activated with a total of 2 ml of chloroformic acid ethyl ester (added in 3 portions) in 40 ml of methylene chloride at -30° C. in the presence of 2.8 ml of triethylamine and 2 drops of 3-dimethylaminopropanol, and the mixture is then combined with a solution of 3.6 g of 7-aminocephalosporanic acid in a mixture of 40 ml of methylene chloride and 3.6 ml of triethylamine. The resulting mixture is then allowed to come to 20° C., after 2 hours the methylene chloride is stripped off, the aqueous solution which remains is washed with ethyl acetate, then acidified (pH 1.5) and extracted with ethyl acetate and the dried organic phase is evaporated in vacuo. The residue is washed with methylene chloride and dried.

Workup

  1. washthe aqueous solution which remains is washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. customthe dried organic phase is evaporated in vacuo
  4. washThe residue is washed with methylene chloride
  5. customdried

Sources & evidence

ORD record
ord-40ca4437e8944fb7a16e09936e76bcaf
Source dataset
uspto-grants-1983_05
Patent number
US04386089

Reaction notes

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