Water → Trisodium 3-acetoxymethyl-7beta-(2-carboxy-2-phenylacetamido)-3-cephem-4-phosphonate

HRID 437861Notes

Reaction equation

HRID 437861 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:17]([NH:18][C:19](=[O:43])[CH:20]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:21]([O:23]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:22])[C:16](=[O:44])[N:10]2[C:11]=1[P:12]([OH:15])(=[O:14])[OH:13])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.O.C([O-])(O)=O.[Na+:65]>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:17]([NH:18][C:19](=[O:43])[CH:20]([C:21]([OH:23])=[O:22])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:16](=[O:44])[N:10]2[C:11]=1[P:12]([O-:15])(=[O:13])[O-:14])(=[O:3])[CH3:2].[Na+:65].[Na+:65].[Na+:65]

Participants

7

Reactant 5

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 7519Anisole2×HCID 516892Sodium BicarbonateHCID 70606535HCID 70606535, compound

Product 1

HCID 131710825Trisodium 3-acetoxymethyl-7beta-(2-carboxy-2-phenylacetamido)-3-cephem-4-phosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One gram of 3-acetoxymethyl-7β-(2-phenyl-2-benzhydryloxycarbonylacetamido)-3-cephem-4-phosphonic acid is dissolved in 2 ml. anisole and treated for two minutes at 0° with 10 ml. trifluoroacetic acid. The mixture is pumped at 0.1 mm at 25° until most of the anisole is removed, and then more anisole is added and pumped off to insure complete removal of TFA. The residue is taken up in 100 ml. water containing three equivalents of NaHCO3, washed with methylene chloride and lyophilized, affording the product, trisodium 3-acetoxymethyl-7β-(2-carboxy-2-phenylacetamido)-3-cephem-4-phosphonate.

Workup

  1. customis pumped at 0.1 mm at 25°
  2. customis removed
  3. additionmore anisole is added
  4. customremoval of TFA

Sources & evidence

ORD record
ord-679ebe3340ac4382b835746b5a49dded
Source dataset
uspto-grants-1977_06
Patent number
US04032521

Reaction notes

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