Hydrochloric Acid → HCID 131710826, compound

HRID 26588Notes

Reaction equation

C([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:17]([NH:18][C:19](=[O:29])[CH:20]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C:21]([OH:23])=[O:22])[C:16](=[O:30])[N:10]2[C:11]=1[P:12]([O-:15])(=[O:14])[O-:13])(=O)C.[Na+:31].[Na+].[Na+].[OH-].[Na+].[Na+].[Cl-].Cl>CCOC(C)=O>[OH:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:17]([NH:18][C:19](=[O:29])[CH:20]([C:24]3[CH:28]=[CH:27][S:26][CH:25]=3)[C:21]([OH:23])=[O:22])[C:16](=[O:30])[N:10]2[C:11]=1[P:12]([O-:15])(=[O:13])[O-:14].[Na+:31].[Na+:31].[Na+:31]

Participants

Conditions

Temperature: 30 °C

Procedure

Trisodium 3-acetoxymethyl-7β-(2-[3-thienyl]-2-carboxyacetamido)-3-cephem-4-phosphonate (1 g.) is dissolved in 100 ml. of a solution of citrus acetyl esterase (J. D. A. Jeffery, et. al., Biochem. J. (1961) 81, 591). The pH is adjusted to 6.6 and the mixture is maintained at 30° C. 1 N NaOH is added dropwise to maintain the pH at 6.6 as the reaction proceeds and the reaction is continued until no further pH change occurs. 10 g. NaCl is added and the mixture is layered with 50 ml. EtOAc, the pH is adjusted to 2.1 with HCl and the mixture is stirred vigorously. The EtOAc layer is separated and washed once with water and then layered with water and stirred and the pH of the aqueous phase is adjusted to 5.9 with 6 N NaOH. The aqueous layer is separated and freeze-dried to give trisodium 3-hydroxymethyl-7β-(2-[3-thienyl]-2-carboxyacetamido)-3-cephem-4-phosphonate.

Workup

temperatureto maintain the pH at 6.6
customas the reaction proceeds
customThe EtOAc layer is separated
washwashed once with water
stirringstirred
customThe aqueous layer is separated
customfreeze-dried

Sources & evidence

ORD record: ord-dd37474b0d26479dabca9c4fe6351ecd
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04150223

Reaction notes

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