p-Toluenesulfonic acid → (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

HRID 129988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129988
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17][C:18]1C=[CH:20][C:21](S(O)(=O)=O)=[CH:22][CH:23]=1.C1N=C[N:30]([C:33](N2C=NC=C2)=[O:34])C=1.N1CCCCCC1>C1COCC1.O>[CH2:10]([O:9][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH:1][C:33]([N:30]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:18][CH2:17]1)=[O:34])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8119AzepaneHCID 682631,1'-CarbonyldiimidazoleHCID 6451313Benzyl L-leucinate

Produkt 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TEA (0.73 ml) was added dropwise to a suspension of Leu-OBzl.TsOH (1.97 g) and CDI (0.85 g) in THF (10 ml) at 0°~5° C. over a period of 5 min and the mixture was stirred at the same temperature for 1 h. Perhydroazepine (0.67 ml) was added and the reaction mixture was stirred at room temperature for 14 h, and poured into water (100 ml). The resulting precipitate was collected by filtration to afford the product (1.75 g).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 14 h
  2. filtrationThe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-843592f2bf9a44f9a4d58a00b072f452
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470833

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