Ethanol → N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine

HRID 1934390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934390
[Li+].[OH-].C([O:5][C:6](=[O:35])[CH2:7][CH2:8][NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:34])/[CH:19]=[CH:20]/[CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:13]1)=[O:11])C.O1CCCC1.C(O)C>O>[C:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][CH:21](/[CH:20]=[CH:19]/[C:18]([N:14]2[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:35])=[O:5])=[O:11])[CH2:13]2)=[O:34])[CH2:26][CH2:25]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70093214N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine ethyl ester

Produkt 1

HCID 70094607N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of LiOH (0.18 g) in water (10 ml) was added to a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine ethyl ester (1.74 g) in the mixture of tetrahydrofuran (10 ml) and ethanol (10 ml) at 0° C. The reaction mixture was stirred for overnight at room temperature, and the solvent was evaporated in vacuo. The residue was resolved in ethyl acetate-water, and acidified with 10% aqueous KHSO4. The whole was washed with water, brine, dried over MgSO4, and evaporated in vacuo to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine as a colorless oil (1.64 g).

Aufarbeitung

  1. customthe solvent was evaporated in vacuo
  2. washThe whole was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dafcb7c7afb54eda93b8893abc13f878
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384028B1

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