Sodium Hydroxide → HCID 21313038, compound

HRID 971621Notes

Reaction equation

HRID 971621 reaction equation
CC(OCC1CS[C@@H]2[C@H](N)C(=O)N2C=1C(O)=O)=O.[OH-].[Na+].[S:21]([CH:25]([C:29]1[CH:33]=[CH:32][S:31][CH:30]=1)[C:26](O)=[O:27])([OH:24])(=[O:23])=[O:22].S(Cl)([Cl:36])=O>CN(C)C=O.CCOCC.O>[S:21]([CH:25]([C:29]1[CH:33]=[CH:32][S:31][CH:30]=1)[C:26]([Cl:36])=[O:27])([OH:24])(=[O:23])=[O:22]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 4413287-Aminocephalosporanic acid2×HCID 21313042HCID 21313042, compound

Product 1

HCID 21313038HCID 21313038, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

With cooling and stirring, 1.84 g. (0.0068 mole) of 7-ACA was suspended in 25 ml. of water and to the suspension was added dropwise 6.8 ml. of a 1N-aqueous solution of sodium hydroxide to dissolve 7-ACA. On the other hand, to a suspension of 1.5 g. (0.0068 mole) of α-sulfo-3-thienylacetic acid in 10 ml. of ether were added 5.5 ml. of thionyl chloride dropwise and 3 drops of dimethylformamide, then the resulting solution was stirred for 5 hours at room temperature. The reaction solution was subjected to the evaporation to dryness under reduced pressure to give α-sulfo-3-thienylacetyl chloride as a residue. The residue was dissolved in 10 ml. of ethyl acetate and the solution was added dropwise to the 7-ACA solution mentioned above, followed by stirring for 30 minutes. The aqueous layer was separated from the reaction solution and adjusted it pH to 6.5 by adding a saturated aqueous solution of NaHCO3. The resulting solution was freeze-dried to obtain 3.6 g. of a crude product. The product was purified according to column chromatography using Amberlite XAD-2 to obtain 1.6 g. (42%) of 7-(α-sulfo-3'-thienylacetamido)cephalosporanic acid.

Workup

  1. temperatureWith cooling
  2. additionOn the other hand, to a suspension of 1.5 g
  3. customThe reaction solution was subjected to the evaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-481eab3631314e34901776fdf138b0ef
Source dataset
uspto-grants-1979_07
Patent number
US04160830

Reaction notes

Loading…