Diisopropylethylamine → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-tert-butoxycarbonyl-3-piperidinol

HRID 1392382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392382
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[OH:15].[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]([NH:27][C:28]1([C:34](O)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:26].OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]([NH:27][C:28]1([C:34]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:3]2[OH:15])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:26]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21874161tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylateHCID 246996681-[(1-Benzofuran-2-carbonyl)amino]cyclohexane-1-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 693100664-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-tert-butoxycarbonyl-3-piperidinolAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of tert-butyl 4-amino-3-hydroxypiperidine-1-carboxylate (20 g, 92 mmol) obtained in step 4 of Preparation Example 1 and 1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarboxylic acid (26 g, 92 mmol) obtained in step 2 of Preparation Example 2 in 150 ml of dimethylformamide, were added hydroxybenzotriazole(HOBt; 24 g, 180 mmol) and diisopropylethylamine (DIEA; 23 g, 180 mmol). The reaction mixture was cooled to 0° C. and was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl; 35 g, 180 mmol) thereto. The reaction mixture was stirred for 4 hours at room temperature, diluted with 300 ml of ethyl acetate, and washed with 10% citric acid solution, a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 30 g of the titled compound.

Aufarbeitung

  1. washwashed with 10% citric acid solution
  2. customThe resulting organic layer was dried
  3. concentrationconcentrated on sodium sulfate
  4. customThe resulting residue was purified with column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5ebd900a0cc84c948f3e0390fd5d1f5e
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342027B2

Notizen zur Reaktion

Wird geladen…