Triethylamine → HCID 178455996, Verbindung

HRID 1655726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655726
[CH2:1]([CH:8]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O)[C:9]([OH:11])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:22][C@@H:23]([CH2:44][C:45]1[N:46]=[CH:47][NH:48][CH:49]=1)[C:24]([NH:26][C@@H:27]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:35])[CH3:34])[CH:31]=[CH2:32])=[O:25].C(N(CC)CC)C.CN(C([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:13][C:12]([CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([NH:22][C@@H:23]([CH2:44][C:45]2[N:46]=[CH:47][NH:48][CH:49]=2)[C:24]([NH:26][C@@H:27]([CH2:37][CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[C@@H:28]([OH:36])[CH2:29][C@@H:30]([CH:33]([CH3:34])[CH3:35])[CH:31]=[CH2:32])=[O:25])=[O:11])=[O:64])=[CH:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 193786602-(RS)-benzyl-4-(4-chlorophenyl)-4-oxo-butyric acidHCID 178456019HCID 178456019, Verbindung

Produkt 1

HCID 178455996HCID 178455996, VerbindungAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.17 g (0.56 mmol) of 2-(RS)-benzyl-4-(4-chlorophenyl)-4-oxo-butyric acid was dissolved in 10 ml of dimethylformamide and treated with 0.20 g (0.51 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide, 0.057 g (0.56 mmol) of triethylamine and 0.21 g (0.56 mmol) of HBTU and stirred at room temperature overnight. The mixture was subsequently evaporated in a high vacuum. The residue was dissolved in ethyl acetate and then washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying the organic phase over sodium sulfate, the solvent was evaporated under reduced pressure and the residue, for purification, was chromatographed on silica gel using a 95:5 mixture of methylene chloride and methanol which contained 0.5% ammonium hydroxide. There were obtained 270 mg (78%) of (S)-α-[(RS)-α-(4-chlorophenylacetyl)hydrocinnamamido]-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide in the form of a yellowish foam. MS: 675 (M+).

Aufarbeitung

  1. customThe mixture was subsequently evaporated in a high vacuum
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialAfter drying the organic phase over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue, for purification
  7. customwas chromatographed on silica gel using
  8. additiona 95:5 mixture of methylene chloride and methanol which

Quellen und Nachweise

ORD-Eintrag
ord-02bfd85972f746b881e3b90f28bbbdbe
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250517

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