Sodium Hydroxide → HCID 178468134, compound

HRID 1763471Notes

Reaction equation

HRID 1763471 reaction equation
[NH2:1][CH:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12.[CH3:28][CH2:29][C:30](Cl)=[S:31].[OH-].[Na+]>C(=O)(O)[O-].[Na+].CC(C)=O>[CH3:28][CH2:29][C:30]([NH:1][C@@H:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([C:9]([CH2:19][PH:20]([OH:22])=[O:21])([S:13][C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][CH2:11][CH3:12])[CH2:7][S:8][C@H:3]12)=[S:31]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21249692Methylthioacetyl chlorideHCID 178468135HCID 178468135, compound

Product 1

HCID 178468134HCID 178468134, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred, cooled (-20°) solution of 11.34 g (0.026 mol) of 7-amino-3-(1-ethoxyhydroxyphosphinylmethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid in 220 ml of 3% sodium bicarbonate and 220 ml of acetone is added dropwise a solution of 3.66 g (0.029 mol) of methylthioacetyl chloride in 52 ml of acetone, during which time the pH of the reaction mixture is maintained at 8.0 by addition of 10% sodium hydroxide. After addition the reaction mixture is stirred an additional 20 minutes at -15°, then is warmed to 25° and extracted with ether. The aqueous phase is passed down a XAD-7 resin column and the product-containing fractions are combined, treated with Amberlite IR-120H ion-exchange resin and lyophilized to yield the title compound.

Workup

  1. additionAfter addition the reaction mixture
  2. temperatureis warmed to 25°
  3. extractionextracted with ether
  4. additiontreated with Amberlite IR-120H ion-exchange resin

Sources & evidence

ORD record
ord-9ab5913d20c64a3499b97a99ea1fd1f6
Source dataset
uspto-grants-1978_09
Patent number
US04112086

Reaction notes

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