反応 #451685

反応方程式

p-Nitrobenzyl 7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylate

→

7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid

収率 78.2%

溶媒

methanol

tetrahydrofuran

反応条件

後処理

1. 1
   その他was subjected to catalytic reduction at room temperature under atmospheric pressure
2. 2
   ろ過The catalyst was filtered off
3. 3
   濃縮the filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONWater (30 ml.) was added to the residue
5. 5
   その他After removing the insoluble substance from the mixture
6. 6
   ろ過by filtration
7. 7
   洗浄the filtrate was washed with ethyl acetate (50 ml.)
8. 8
   workup.ADDITIONEthyl acetate (70 ml.) was added to the solution
9. 9
   その他After the ethyl acetate layer was removed
10. 10
    抽出the aqueous layer was extracted with ethyl acetate (30 ml.) twice
11. 11
    洗浄washed with a saturated aqueous solution of sodium chloride
12. 12
    乾燥dried over magnesium sulfate
13. 13
    濃縮concentrated under reduced pressure

実験手順

p-Nitrobenzyl 7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylate (syn isomer, 0.8 g.) was dissolved in a mixed solution of methanol (30 ml.) and tetrahydrofuran (60 ml.). After adding 10% palladium carbon (0.4 g.) to the solution, the mixture was subjected to catalytic reduction at room temperature under atmospheric pressure. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Water (30 ml.) was added to the residue and the mixture was adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. After removing the insoluble substance from the mixture by filtration, the filtrate was washed with ethyl acetate (50 ml.). Ethyl acetate (70 ml.) was added to the solution, and the mixture was adjusted to pH 1.5 with 10% hydrochloric acid and then shaked sufficiently. After the ethyl acetate layer was removed, the aqueous layer was extracted with ethyl acetate (30 ml.) twice. The ethyl acetate layer and the extracts were combined together, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then concentrated under reduced pressure to give 7-{2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido}-3-chloro-3-cephem-4-carboxylic acid (syn isomer 0.48 g.), m.p. 165° to 174° C. (dec.).

出典