Hydrochloric Acid → HCID 131710826, compound

HRID 437862Notes

Reaction equation

HRID 437862 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+].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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131710827HCID 131710827, compound

Product 1

HCID 131710826HCID 131710826, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. temperatureto maintain the pH at 6.6
  2. customas the reaction proceeds
  3. additionNacl is added
  4. customThe EtOAc layer is separated
  5. washwashed once with water
  6. stirringstirred
  7. customThe aqueous layer is separated
  8. customfreeze-dried

Sources & evidence

ORD record
ord-84487e50decc4375bfe62a632210b8c1
Source dataset
uspto-grants-1977_06
Patent number
US04032521

Reaction notes

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