Sodium Carbonate → 7-[2-(2-Formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-cephem-4-carboxylic acid

2-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 1.2 g.), N,N-dimethylformamide (0.768 g.), phosphoryl chloride (1.61 g.) and tetrahydrofuran (2.4 ml.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. A suspension of 7-amino-3-cephem-4-carboxylic acid (0.89 g.) in a mixture of tetrahydrofuran (8.9 ml.), acetone (4.5 ml.) and water (4.5 ml.) was adjusted to pH 7 to 8 with 20% aqueous sodium carbonate. The activated acid solution was added to the solution at -5° to 0° C. while keeping at pH 7 to 8 and stirred at the same temperature for 30 minutes. The resultant solution was concentrated in vacuo, and water and ethyl acetate were added to the residue. The solution was adjusted to pH 2.5 and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was pulverized with diethyl ether, collected by filtration and dried to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.95 g).

1. customto give an activated acid solution
2. additionThe activated acid solution was added to the solution at -5° to 0° C.
3. concentrationThe resultant solution was concentrated in vacuo, and water and ethyl acetate
4. additionwere added to the residue
5. extractionextracted with ethyl acetate
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. filtrationcollected by filtration
10. customdried

ORD 기록

ord-319527bb9561427c9315450b2012e40d

출처 데이터셋

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04598147