Triethylamine → N-[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide

HRID 409585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409585
Cl.[C:2]1([C@H:12]([NH:14][C@H:15]2[CH2:19][CH2:18][N:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:16]2)[CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:30][O:31][C:32](=[O:36])[C@H:33]([CH3:35])[NH2:34].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.O>[CH3:30][O:31][C:32]([C@@H:33]([NH:34][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([N:17]2[CH2:18][CH2:19][C@H:15]([NH:14][C@@H:12]([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:5]=[CH:4][CH:3]=3)[CH3:13])[CH2:16]2)=[CH:21][CH:22]=1)[CH3:35])=[O:36]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733257Alanine methyl ester hydrochlorideHCID 674072274-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzoic acid hydrochloride

Produkt 1

HCID 58973534N-[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamideAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 150 mg of 4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzoic acid hydrochloride of Example 3.001 and 58 mg of (1)-alanine methyl ester hydrochloride in 5 ml of DMF were added 163 mg of 1-[3-(dimethylaminopropyl)]-3-ethylcarbodiimide hydrochloride, 115 mg of 1-hydroxybenzotriazole and 125 μl of triethylamine, and the reaction mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and ethyl acetate, the mixture was stirred and then the liquids were separated. The organic layer was dried and concentrated under reduced pressure, then, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=65:35→35:65) to obtain 31.9 mg of N—[(S)-1-methoxycarbonylethyl]-4-[(S)-3-[(R)-1-(naphthalen-1-yl)ethylamino]pyrrolidin-1-yl]benzamide.

Aufarbeitung

  1. stirringthe mixture was stirred
  2. customthe liquids were separated
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=65:35→35:65)

Quellen und Nachweise

ORD-Eintrag
ord-126c4970d9fd4d029192cc7e9ff9c103
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759387B2

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