Sodium Hydroxide → HCID 131711130, compound

HRID 839928Notes

Reaction equation

HRID 839928 reaction equation
O1C=C[CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[S:8].[C:10](=[O:13])(O)[O-].[Na+].[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21][C:22]([NH:24][CH:25]2[C:40](=[O:41])[N:27]3[C:28]([C:37]([O-:39])=[O:38])=[C:29]([CH2:32]OC(=O)C)[CH2:30][S:31][C@H:26]23)=O)[N:20]=1.[Na+].[OH-:43].[Na+]>O.C(O)(=O)C>[NH2:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21][C:22]([NH:24][CH:25]2[C:40](=[O:41])[N:27]3[C:28]([C:37]([OH:39])=[O:38])=[C:29]([CH2:32][S:8][C:7]([C:6]4[O:13][CH:10]=[CH:3][CH:2]=4)=[O:9])[CH2:30][S:31][C@H:26]23)=[O:43])[N:20]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 88702478HCID 88702478, compoundHCID 178526161HCID 178526161, compound

Product 1

HCID 131711130HCID 131711130, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture of 0.25 g of 2-furyl-thioacetic acid, 4 ml of distilled water, 0.17 mg of sodium bicarbonate and 0.435 mg of the salt of Step A was held at 50° C for 5 hours and was then cooled to room temperature. The mixture was adjusted to a pH of 3-4 with acetic acid and was vacuum filtered. The recovered product was rinsed and dried to obtain 420 mg of raw product. The latter was dissolved in water containing sodium hydroxide and the solution was passed through an ion exchange resin column. Elution was with water and then with water containing 10% of isopropanol and the fractions with the product were combined and the solvents were evaporated under reduced pressure. The aqueous residue was acidified with acetic acid to obtain 115 mg of 7-[-(2-amino-4-thiazolyl)-acetamido]-3-[{(2-furyl)-carbonyl}thiomethyl]-ceph-3-eme-4-carboxylic acid.

Workup

  1. filtrationfiltered
  2. washThe recovered product was rinsed
  3. customdried
  4. customto obtain 420 mg of raw product
  5. washElution
  6. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-de01c7c0ffe742b7b80133536f1caddb
Source dataset
uspto-grants-1978_06
Patent number
US04097595

Reaction notes

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