Sodium Hydroxide → [[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid

HRID 1246751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246751
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:14]([NH:16][CH2:17][C:18]([O:20]CC2C=CC=CC=2)=[O:19])=[O:15])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15])=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86592300benzyl [[(2S)-2-[[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]-acetate

Produkt 1

HCID 69379045[[(2S)-2-[[(2E)-3-(4-Chlorophenyl)-2-propenoyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acidAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of benzyl {[(2S)-2-{[(2E)-3-(4-chlorophenyl)-2-propenoyl]amino}-3-(2-pyridyl)propanoyl]amino}-acetate (10.8 g) in methanol (200 ml) was added 1N aqueous sodium hydroxide solution (22.6 ml), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo, and the residue was treated with aqueous citric acid solution (10%, 100 ml). The resulting white precipitate was collected by filtration, washed with tetrahydrofuran-hexane (1:1, 150 ml), and dried in vacuo to give the title compound (8.25 g) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was treated with aqueous citric acid solution (10%, 100 ml)
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with tetrahydrofuran-hexane (1:1, 150 ml)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-778e76df442c4788b01a06d8f6e8dcd8
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129243B2

Notizen zur Reaktion

Wird geladen…