Methanol → HCID 13559600, compound

HRID 2309252Notes

Reaction equation

HRID 2309252 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH:9]([CH2:13][CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[C:10]([OH:12])=[O:11])=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:30]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:13][CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[C:10]([O:12][CH3:30])=[O:11])=[O:7])=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 13393254HCID 13393254, compound

Product 1

HCID 13559600HCID 13559600, compound

Procedure

19 Grams of 2-(4-chlorobenzoylamino)-3-(oxindol3-yl)propionic acid 1/4-hydrate prepared in Example 3 was dissolved in 30 ml of methanol, then to this solution was added dropwise 9.4 g of thionyl chloride under an ice-cooled condition, then the reaction mixture was stirred at a room temperature overnight. Methanol was removed by evaporation, the residue thus obtained was extracted with chloroform, and the extract was dried with anhydrous sodium sulfate, then the solvent was removed by evaporation. The resulting residue was purified by means of a silica gel column chromatography (eluting agent: chloroform/methanol=40/1) to obtain 10.5 g of methyl 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionate. The chemical structure of this product was determined by means of NMR method.

Workup

  1. temperaturecooled condition
  2. customMethanol was removed by evaporation
  3. customthe residue thus obtained
  4. extractionwas extracted with chloroform
  5. dry with materialthe extract was dried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation
  7. customThe resulting residue was purified by means of a silica gel column chromatography (eluting agent: chloroform/methanol=40/1)

Sources & evidence

ORD record
ord-38025371600847438c35f9aad137e421
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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