Triethylamine → HCID 118162494, Verbindung

HRID 707504

Reaktionsgleichung

Reaktionsgleichung von HRID 707504
[CH2:1]([O:3][CH:4]([O:15][CH2:16][CH3:17])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=1)[CH3:2].[C:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C@H:30]([NH:34][C:35]([O:37][CH2:38][CH:39]2[C:51]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[C:45]3[C:40]2=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:36])[C:31](O)=[O:32])=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(OCC)(=O)C.O.CN(C=O)C>[C:18]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][C@H:30]([NH:34][C:35](=[O:36])[O:37][CH2:38][CH:39]2[C:51]3[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=3[C:45]3[C:40]2=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:31](=[O:32])[N:6]([CH2:5][CH:4]([O:15][CH2:16][CH3:17])[O:3][CH2:1][CH3:2])[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[N:9]=2)=[CH:27][CH:28]=1)([CH3:21])([CH3:19])[CH3:20]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10895791Fmoc-L-Tyr(tBu)-OHHCID 118162514HCID 118162514, Verbindung

Produkt 1

HCID 118162494HCID 118162494, VerbindungAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixed solution of (2,2-diethoxyethyl)((6-fluoropyridin-2-yl)methyl)amine (514 mg, 2.12 mmol) described in Production Example 1-1-1 and DMF (10 mL) were added a commercially available product of (2S)-3-(4-(tert-butoxy)phenyl)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)propanoic acid (886 mg, 2.12 mmol), triethylamine (355 μL, 2.54 mmol) and HATU (968 mg, 2.54 mmol) at room temperature. The resultant mixture was stirred at room temperature for 45 minutes. Water was added to the reaction mixture, and the resultant mixture was then extracted with ethyl acetate. An organic layer was washed with water and saturated brine, was then dried over anhydrous magnesium sulfate, and was then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 and then ethyl acetate) to give the title compound (1.37 g, yield: 94%).

Aufarbeitung

  1. extractionthe resultant mixture was then extracted with ethyl acetate
  2. washAn organic layer was washed with water and saturated brine
  3. dry with materialwas then dried over anhydrous magnesium sulfate
  4. filtrationwas then filtrated
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (heptane

Quellen und Nachweise

ORD-Eintrag
ord-b8c22beff66548f59055a5b181382984
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174998B2

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