Diisopropylethylamine → (9H-Fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylcarbamate

HRID 1254502

Reaktionsgleichung

Reaktionsgleichung von HRID 1254502
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[C@@H:5]([NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:6])[CH3:2].[NH:22]([C:28]([O:30][CH2:31][CH:32]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29])[C@H:23]([C:25](O)=[O:26])[CH3:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C.O>[CH2:20]([O:19][CH:4]([O:3][CH2:1][CH3:2])[C@@H:5]([N:7]([CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[C:25](=[O:26])[C@@H:23]([NH:22][C:28](=[O:29])[O:30][CH2:31][CH:32]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=2[C:39]2[C:44]1=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:24])[CH3:6])[CH3:21]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67075196(S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine

Produkt 1

HCID 86652577(9H-Fluoren-9-yl)methyl(S)-1-(((S)-1,1-diethoxypropan-2-yl)(naphthalen-1-ylmethyl)amino)-1-oxopropan-2-ylcarbamateAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

According to the procedure described in the synthesis method of Compound III-1, (S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine (Compound IX-2) 12.9 g (45 mmol) and Fmoc-Ala-OH 18.3 g (58.8 mmol) were dissolved in DMF (200 ml). HATU (O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (25.6 g, 67.5 mmol) and DIEA (diidopropylethylamine) (8.7 g, 67.5 mmol) were added at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into water (800 ml). The solution was extracted with EA (ethyl acetate) (300 ml×3). The combined extracts were dried over Na2SO4 and then filtered. The solvent was removed in vacuo. The residue was purified by column chromatography on silica gel with PE (petroleum ether): EA=30:1 to 5:1 to give the title compound 18.6 g, (yield 71%).

Aufarbeitung

  1. extractionThe solution was extracted with EA (ethyl acetate) (300 ml×3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel with PE (petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-985edd7f69d542948c0927070ea2cd51
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455488B2

Verknüpfte Notizen

Wird geladen…