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 1588328Notes

Reaction equation

HRID 1588328 reaction equation
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+]>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]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 446570Glutaryl-7-aminocephalosporanic acid2×

Product 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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Glutaryl 7ACA (3.0 g) is slurried in 45 ml water and the pH is adjusted to 6.0 with 20% sodium hydroxide to dissolve the glutaryl 7ACA. Yeast esterase (0.3 g) is added and the solution is stirred at 22°-25° C. for 4 hours while maintaining the pH at 5.9-6.1 with 20% sodium hydroxide. The yield by HPLC to desacetyl glutaryl 7ACA is 98% with the ratio of desacetyl glutaryl 7ACA to glutaryl 7ACA >99%. The resulting solution is filtered with filter aid to remove the yeast and aliquots are used for subsequent chemical conversions of desacetyl glutaryl 7ACA to glutaryl 7ACA. The solution may be stored frozen.

Workup

  1. additionYeast esterase (0.3 g) is added

Sources & evidence

ORD record
ord-55618526b7794c16bf0de53644fe10ed
Source dataset
uspto-grants-1993_06
Patent number
US05221739

Reaction notes

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