Hydrochloric Acid → 3-Desacetyl Cefotaxime Sodium SaltDISCONTINUED, offer D295530

HRID 1073811ノート

反応式

HRID 1073811 の反応式
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]12.C(=O)([O-])O.[Na+:20].Cl.ClCC([NH:26][C:27]1[S:28][CH:29]=[C:30](/[C:32](=[N:36]/[O:37][CH3:38])/[C:33](Cl)=[O:34])[N:31]=1)=O.Cl.CNC(=S)[S-].[Na+]>C(OCC)(=O)C.O.C1COCC1>[NH2:26][C:27]1[S:28][CH:29]=[C:30](/[C:32](=[N:36]/[O:37][CH3:38])/[C:33]([NH:1][C@@H:2]2[C:14](=[O:15])[N:4]3[C:5]([C:11]([O-:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]23)=[O:34])[N:31]=1.[Na+:20]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5366415Metam-sodiumHCID 11031679(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 12884125(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochloride

生成物 1

HCID 236762833-Desacetyl Cefotaxime Sodium SaltDISCONTINUED, offer D295530収率 55.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In 500 ml of a (1:1) mixture of water and THF was suspended 11.9 g of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid, and 19.4 g of sodium hydrogencarbonate was added under ice-cooling and stirring. To the suspension was added 20.6 g of 2-(2-chloroacetamidothiazol-4-yl)-(Z)-2-methoxyiminoacetyl chloride hydrochloride, followed by stirring for 30 minutes. The reaction mixture was shaken with 100 ml of water and 150 ml of ethyl acetate. The aqueous layer was taken and adjusted to pH 7.0 with 1N-hydrochloric acid under ice-cooling and stirring. To the mixture was gradually added 12.0 g of sodium N-methyldithiocarbamate at room temperature under stirring to remove the amino group. After shaking with 200 ml of ethyl acetate, the aqueous layer was taken and concentrated to 50 ml under reduced pressure. The residue was subjected to a column chromatography on XAD-II (1.2l) eluting with water. The fractions containing the objective compound were collected, concentrated under reduced pressure, and then lyophilized to give 12.4 g of sodium 7β-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate as pale yellow powders.

後処理

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringby stirring for 30 minutes
  4. temperaturecooling
  5. stirringstirring
  6. customat room temperature
  7. stirringunder stirring
  8. customto remove the amino group
  9. stirringAfter shaking with 200 ml of ethyl acetate
  10. concentrationconcentrated to 50 ml under reduced pressure
  11. washeluting with water
  12. additionThe fractions containing the objective compound
  13. customwere collected
  14. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-30b3fb09926f40758fbf320b0728c48f
出典データセット
uspto-grants-1990_11
特許番号
US04971963

反応ノート

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