1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-beta-alanine methyl ester

HRID 1934393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934393
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@@H:5]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH2:6].[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30](/[CH:33]=[CH:34]/[C:35]([N:37]2[CH2:42][CH2:41][CH2:40][C@@H:39]([C:43](O)=[O:44])[CH2:38]2)=[O:36])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@@H:5]([CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[NH:6][C:43]([C@@H:39]1[CH2:40][CH2:41][CH2:42][N:37]([C:35](=[O:36])/[CH:34]=[CH:33]/[CH:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:26])[CH2:28][CH2:29]2)[CH2:38]1)=[O:44]

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69817990(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acidHCID 867580313(R)-(3,4-dimethoxyphenethyl)-beta-alanine methyl ester

Produkt 1

HCID 86758030N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-beta-alanine methyl esterAusbeute 91,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3(R)-(3,4-dimethoxyphenethyl)-β-alanine methyl ester (0.87 g), (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid (1.19 g) and 1-hydroxybenztriazole (0.44 g) in dimethylformamide (9 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.59 ml) at 0° C. The reaction mixture was stirred overnight at room temperature, and then poured into water. The whole was extracted with ethyl acetate, washed with aqueous saturated NaHCO3, water, and brine, dried over MgSO4, and evaporated in vacuo, subsequently. The residue was purified by column chromatography on silica gel eluting with ethyl acetate: n-hexane=(5:1) to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-3(R)-(3,4-dimethoxyphenethyl)-β-alanine methyl ester as a colorless oil (1.83 g).

Aufarbeitung

  1. extractionThe whole was extracted with ethyl acetate
  2. washwashed with aqueous saturated NaHCO3, water, and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-60d4fa9d85a64369a5c1d2c922d42e41
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384028B1

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