Hydrochloric Acid → HCID 70606535, compound

HRID 437860Notes

Reaction equation

HRID 437860 reaction equation
[NH2:1][C@@H:2]1[C:18](=[O:19])[N:4]2[C:5]([P:14]([O-:17])(=[O:16])[O-:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@H:3]12.[Na+].[Na+].C([O-])(O)=O.[Na+].[C:27]1([CH:33]([C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[C:34](Cl)=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>CCOC(C)=O.O.CC(C)=O>[C:11]([O:10][CH2:9][C:6]1[CH2:7][S:8][C@@H:3]2[C@H:2]([NH:1][C:34](=[O:35])[CH:33]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:37]([O:39][CH:40]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])[C:18](=[O:19])[N:4]2[C:5]=1[P:14]([OH:17])(=[O:15])[OH:16])(=[O:13])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20472690HCID 20472690, compoundHCID 70606905HCID 70606905, compound

Product 1

HCID 70606535HCID 70606535, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 10 mmoles of disodium 7β-amino-3-acetoxymethyl-3-cephem-4-phosphonate in 100 ml. water and 100 ml. acetone containing 5 g. NaHCO3 is added 20 mmoles of 2-phenyl-2-benzhydryloxycarbonylacetyl chloride in 40 ml. acetone at 0° C. After 1 hour stirring at 0° and 2 hours at 25° 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, dried with MgSO4, filtered and evaporated, affording the product, 3-acetoxymethyl-7β-(2-phenyl-2-benzhydryloxycarbonylacetamido)-3-cephem-4-phosphonic acid.

Workup

  1. customat 0° C
  2. additionthe aqueous solution added to 100 ml
  3. customthe ethyl acetate layer separated
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-4f2f6e4dc39846a39279c9b50a733fe3
Source dataset
uspto-grants-1977_06
Patent number
US04032521

Reaction notes

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