2-Thiopheneacetic acid → 3-Methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid

HRID 1287992Notes

Reaction equation

HRID 1287992 reaction equation
[NH2:1][CH:2]1[C:16](=[O:17])[N:4]2[C:5]([C:13]([OH:15])=[O:14])=[C:6]([CH:9]=[N:10][O:11][CH3:12])[CH2:7][S:8][C@H:3]12.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[CH2:23][C:24](Cl)=[O:25].S1C=CC=C1CC(O)=O.S(Cl)(Cl)=O>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[CH3:12][O:11][N:10]=[CH:9][C:6]1[CH2:7][S:8][C@@H:3]2[CH:2]([NH:1][C:24](=[O:25])[CH2:23][C:19]3[S:18][CH:22]=[CH:21][CH:20]=3)[C:16](=[O:17])[N:4]2[C:5]=1[C:13]([OH:15])=[O:14]

Participants

8

Reactant 4

HCID 159702-Thiopheneacetic acidHCID 24386Thionyl ChlorideHCID 1623622-Thiopheneacetyl chlorideHCID 1317104987-Amino-3-methoxyiminomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317104973-Methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acidYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 7-amino-3-methoxyiminomethyl-3-cephem-4-carboxylic acid (134 mg) and triethylamine (0.1 ml) in chloroform (1 ml) is added 2-thienylacetyl chloride prepared from 2-thienylacetic acid (78 mg) and thionyl chloride (0.1 ml) in chloroform (1 ml), and the mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with water, adjusted to pH 2, and extracted with ethyl acetate. The extract solution is washed with water, dried and evaporated under reduced pressure. Treatment of the residue with ether gives 3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4 -carboxylic acid (161 mg; 82%). m.p. 186°-189° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract solution is washed with water
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5165454bc925489a852fe86a69748b20
Source dataset
uspto-grants-1976_10
Patent number
US03987039

Reaction notes

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