Diisopropylethylamine → (9H-fluoren-9-yl)methyl(S)-1-((S)-(1,1-diethoxypropan-2-yl)(benzyl)amino)-1-oxopropan-2-ylcarbamate

HRID 576869

Reaktionsgleichung

Reaktionsgleichung von HRID 576869
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH3:23])[C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH2:48]([NH:55][C@@H:56]([CH3:64])[CH:57]([O:61][CH2:62][CH3:63])[O:58][CH2:59][CH3:60])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH2:62]([O:61][CH:57]([O:58][CH2:59][CH3:60])[C@@H:56]([N:55]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:20](=[O:21])[C@@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH3:23])[CH3:64])[CH3:63]

Komponenten

7

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 66978105(S)-N-benzyl-1,1-diethoxypropan-2-amine2×

Produkt 1

HCID 86663942(9H-fluoren-9-yl)methyl(S)-1-((S)-(1,1-diethoxypropan-2-yl)(benzyl)amino)-1-oxopropan-2-ylcarbamateAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanoic acid 68 mg (0.22 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate 84 mg (0.22 mmol) in dichloromethane 1 ml, a solution of (S)—N-benzyl-1,1-diethoxypropan-2-amine (Compound IV-15) 47 mg (0.2 mmol) and N,N′-diisopropylethylamine 38 ml (0.22 mmol) in dichloromethane 1 ml was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated aqueous sodium bicarbonate 50 ml, water 50 ml and brine 50 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=9:1 to 7:3) to obtain the title compound 48 mg (45%).

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate 50 ml, water 50 ml and brine 50 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=9:1 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-7da1a46a181d46ccbd34358cbf58d52e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040531B2

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