4-Methylmorpholine → 2-acetylamino-N-[2-[2-(2-cyanoethyl)-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide

HRID 8526

Reaktionsgleichung

Reaktionsgleichung von HRID 8526
[NH2:1][CH:2]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH:6]1[CH2:24][CH2:25][C:26]#[N:27])=[O:4].[C:36]([NH:39][C@H:40]([C:49](O)=[O:50])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=1)(=[O:38])[CH3:37].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)CCCN=C=NCC>CN(C=O)C.O>[C:36]([NH:39][CH:40]([CH2:41][C:42]1[CH:43]=[CH:44][C:45]([OH:48])=[CH:46][CH:47]=1)[C:49]([NH:1][CH:2]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:3]([N:5]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:7][CH:6]1[CH2:24][CH2:25][C:26]#[N:27])=[O:4])=[O:50])(=[O:38])[CH3:37]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68310N-Acetyl-L-tyrosineHCID 757711-HydroxybenzotriazoleHCID 220156953-[1-[2-Amino-3-(4-fluorophenyl)propionyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-2-yl]propionitrile

Produkt 1

HCID 220156872-acetylamino-N-[2-[2-(2-cyanoethyl)-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-1-yl]-1-(4-fluorobenzyl)-2-oxo-ethyl]-3-(4-hydroxyphenyl)-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-[1-[2-amino-3-(4-fluorophenyl)proponyl]-4-(2-naphthalen-2-ylethyl)-5-oxo-piperazin-2-yl]propionitrile, 33, (47.2 g, 100 mmol), N-acetyl-L-tyrosine (22.3 g, 120 mmol), 1-hydroxybenzotriazole (16.2 g, 120 mmol), and N-methylmorpholine (132 mL, 120 mmol) in DMF (150 mL) is cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (24.9 g, 130 mmol) is slowly added. The resulting mixture is stirred for 2 hours at 0° C. then allowed to warm and stir at room temperature another 2 hours. The reaction solution is diluted with water and the resulting solid is collected by filtration, re-dissolved in EtOAc and extracted with water, dried and concentrated in vacuo to afford the crude product which is purified over silica gel.

Aufarbeitung

  1. temperatureto warm
  2. stirringstir at room temperature another 2 hours
  3. filtrationthe resulting solid is collected by filtration
  4. dissolutionre-dissolved in EtOAc
  5. extractionextracted with water
  6. customdried
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8bd411e3c3ab4b63b8ed399336f16009
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087759B2

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