Diisopropylethylamine → methyl (S)-alpha-[(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamamido]imidazolepropionate

HRID 274773

Reaktionsgleichung

Reaktionsgleichung von HRID 274773
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6](CC1N=CNC=1)[NH2:7].[C:15]([S:19]([CH2:22][C@@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]([OH:26])=O)(=[O:21])=[O:20])([CH3:18])([CH3:17])[CH3:16].F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CC[N:63]([CH:67]([CH3:69])C)[CH:64]([CH3:66])C>C(#N)C>[C:15]([S:19]([CH2:22][C@@H:23]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]([NH:7][C@@H:6]([CH2:69][C:67]1[NH:41][CH:66]=[CH:64][N:63]=1)[C:5]([O:4][CH3:3])=[O:14])=[O:26])(=[O:20])=[O:21])([CH3:16])([CH3:17])[CH3:18]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 9860623(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamic acidHCID 178419105HCID 178419105, Verbindung

Produkt 1

HCID 67931045methyl (S)-alpha-[(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamamido]imidazolepropionateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

15.8 g (65.5 mmol) of L-histidine methyl ester dihydrochloride, 18.6 g of (S)-α-[(t-butylsulphonyl)-methyl]hydrocinnamic acid, 28.9 g of BOP and 35.8 ml of Hunig base are dissolved in 400 ml of acetonitrile and subsequently stirred at room temperature for 12 hours. After the usual working-up the crude produce is purified by flash chromatography on silica gel, whereby there are obtained 28 g (98%) of methyl (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]imidazolepropionate as a resin, Rf value 0.25 in a 20:1 mixture of methylene chloride and methanol, MS: 435 (M)+.

Aufarbeitung

  1. customproduce
  2. customis purified by flash chromatography on silica gel, whereby there

Quellen und Nachweise

ORD-Eintrag
ord-18fcda8f5c094b50b628d3ec77436338
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389616

Verknüpfte Notizen

Wird geladen…