Diethyl Ether → HCID 13393254, compound

HRID 2309240Notes

Reaction equation

HRID 2309240 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17])[C:4]([OH:6])=[O:5].C1(N=C=NC2CCCCC2)CCCCC1.[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=1.CCOCC>O1CCOCC1.C(Cl)(Cl)Cl>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:2][CH:3]([CH2:7][CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[C:4]([OH:6])=[O:5])=[O:39])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 63184-Chlorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Product 1

HCID 13393254HCID 13393254, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

1.14 Grams of 2-amino-3-(oxindol-3-yl)propionic acid hydrochloride prepared in Reference Example 1, 1.3 g of dicyclohexylcarbodiimide (DCC) and 1.0 g of p-chlorobenzoic acid were suspended in 10 ml of dioxane, then the suspension was stirred at 60°-70° C. for 5 hours. After the reaction was completed, the solvent was removed by evaporation, to the residue thus obtained was added ether, and the crystals formed were removed by filtration. The filtrate obtained was concentrated, then the residue thus obtained was dissolved by adding chloroform, the chloroform solution was washed with water and a saturated sodium chloride aqueous solution. The chloroform solution was dried with anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was recrystallized from methanol-water to obtain 290 mg of 2-(4-chlorobenzoylamino)-3-(oxindol-3-yl)propionic acid 1/4-hydrate in the form of colorless powdery substance. Melting

Workup

  1. customthe solvent was removed by evaporation, to the residue
  2. customthus obtained
  3. customthe crystals formed
  4. customwere removed by filtration
  5. customThe filtrate obtained
  6. concentrationwas concentrated
  7. customthe residue thus obtained
  8. dissolutionwas dissolved
  9. washthe chloroform solution was washed with water
  10. dry with materialThe chloroform solution was dried with anhydrous sodium sulfate
  11. customthe solvent was removed by evaporation
  12. customThe residue was recrystallized from methanol-water

Sources & evidence

ORD record
ord-bb0f7157006a4688abc05dff74bf072b
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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