Hydrochloric Acid → Disodium 7beta-(2-furylacetamido)-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate

HRID 26587Notes

Reaction equation

HRID 26587 reaction equation
[NH2:1][C@@H:2]1[C:21](=[O:22])[N:4]2[C:5]([P:17]([O-:20])(=[O:19])[O-:18])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.C([O-])(O)=O.[Na+:27].[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34](Cl)=[O:35].Cl>CC(C)=O.CCOC(C)=O.O>[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][C:34]([NH:1][C@@H:2]1[C:21](=[O:22])[N:4]2[C:5]([P:17]([O-:18])(=[O:20])[O-:19])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12)=[O:35].[Na+:27].[Na+:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 75975Furan-2-acetyl chlorideHCID 516892Sodium BicarbonateHCID 1317114837beta-amino-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate

Product 1

HCID 70606401Disodium 7beta-(2-furylacetamido)-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent3×HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 mmoles 7β-amino-3-(N-methyltetrazolylthiomethyl)-3-cephem-4-phosphonate in 100 ml. water and 100 ml. acetone containing 5 g. NaHCO3 is added 20 mmoles 2-furylacetyl chloride in 40 ml acetone at 0° C. After 1 hr. stirring at 0° and 2 hrs at 25° the acetone is pumped off in vacuo and the aqueous solution added to 100 ml. water and 200 ml. EtOAc. The pH is adjusted to 2 with HCl and the ethyl acetate layer separated, and evaporated. The residue is taken up in 50 ml water containing 1.6 g. NaHCO3 and lyophilized, providing the title compound.

Workup

  1. additionthe aqueous solution added to 100 ml
  2. customthe ethyl acetate layer separated
  3. customevaporated

Sources & evidence

ORD record
ord-2597a13f2a1849b4a8a94d6abd6618e3
Source dataset
uspto-grants-1979_04
Patent number
US04150223

Reaction notes

Loading…