Water → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamide

HRID 2394321

Reaktionsgleichung

Reaktionsgleichung von HRID 2394321
CN1CCOCC1.Cl.[C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH:17]([NH:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:25])[CH3:24])[NH2:22])[CH3:18])=[CH:13][CH:12]=1)#[N:10].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35](OC)[CH:34]=1)=[O:31].O>C(Cl)Cl>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH:17]([NH:19][C:20](=[O:26])[C@H:21]([CH:23]([CH3:24])[CH3:25])[NH:22][C:30]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])[CH3:18])=[CH:27][CH:28]=1)#[N:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 220191803-Methoxyphenyl carbonochloridateHCID 22866849N1-[2-(4-cyanophenoxy)-1-methylethyl]L-valinamide hydrochloride

Produkt 1

HCID 53713420N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-phenoxycarbonyl-L-valinamideAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.0 g of N-methylmorpholine was added to a solution containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide hydrochloride dissolved in 100 ml of methylene chloride, at -20° C. After 0.9 g of 3-methoxyphenyl chloroformate was added to the mixture at -20° C., the reaction mixture was allowed to sit and warm naturally to room temperature while being stirred. The whole mixture was stirred for 2 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 0.25 g of the desired product in the form of a white plated crystal (yield: 12%).

Aufarbeitung

  1. stirringThe whole mixture was stirred for 2 hours at room temperature
  2. washAfter the methylene chloride layer was washed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe methylene chloride was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a8975b2b51594056ad5e9bacda32a3b1
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811424

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