Sodium Hydroxide → (6R,7R)-7-((4-Carboxy-1-oxobutyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

HRID 1588329ノート

反応式

HRID 1588329 の反応式
CC([O:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([OH:26])=[O:25])=O.[OH-].[Na+].[Cl-].[Ca+2].[Cl-]>O>[CH2:23]1[S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:15])[C:11](=[O:12])[N:8]2[C:7]([C:24]([OH:26])=[O:25])=[C:6]1[CH2:5][OH:4]

参加物

5

反応物 3

HCID 14798Sodium Hydroxide3 回HCID 446570Glutaryl-7-aminocephalosporanic acid2 回HCID 5284359Calcium Chloride

生成物 1

HCID 6453255(6R,7R)-7-((4-Carboxy-1-oxobutyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid収率 83%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Glutaryl 7ACA (4.0 g) is slurried in 60 ml water and the pH is adjusted to 3.5 to 4.0 with 20% sodium hydroxide to dissolve the glutaryl 7ACA. To the solution is added 2.2 g calcium chloride and the pH is adjusted to 5.5 to 6.0 with 20% sodium hydroxide. Yeast esterase (0.4 g) is added and the solution is stirred at 22°-25° C. for 2.5 hours while maintaining the pH at 5.9-6.1 with 20% sodium hydroxide. The yield by HPLC to desacetyl glutaryl 7ACA is 97% with the ratio of desacetyl glutaryl 7ACA to glutaryl 7ACA >99%. The resulting solution is filtered with filter aid to remove the yeast and is diluted with water to 90 ml. Desacetyl glutaryl 7ACA calcium salt is precipitated by the addition of 450 ml ethanol. The crystals are filtered, washed with ethanol, and dried. Subsequent crystals which come out in the filtrate are similarly filtered and dried. (Crystal purity as desacetyl glutaryl 7ACA is 63%). The crystallization yield is 83%. The desacetyl glutaryl 7ACA calcium salt was characterized by NMR and IR:

後処理

  1. additionYeast esterase (0.4 g) is added

出典と根拠

ORDレコード
ord-90307882f3e249fe9214f1ca351ba2ce
出典データセット
uspto-grants-1993_06
特許番号
US05221739

反応ノート

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