4-Methylmorpholine → 4-[N'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester

HRID 1401818

Reaktionsgleichung

Reaktionsgleichung von HRID 1401818
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][NH2:17])=[O:15])[CH:5]=[CH:4][C:3]1=2.[C:19]([N:26]1[CH2:31][CH2:30]N(C(O)=O)[CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CC[O:62][CH2:61][CH2:60]1>CN(C=O)C.O>[C:22]([O:21][C:19]([N:26]1[CH2:27][CH2:28][CH:60]([C:61]([NH:17][NH:16][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:18])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=3[CH:7]=2)=[O:15])=[O:62])[CH2:30][CH2:31]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 190015635,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbohydrazideHCID 219560274-(Tert-butoxycarbonyl)piperazine-1-carboxylic acid

Produkt 1

HCID 683807944-[N'-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)hydrazinocarbonyl]piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.2 g (6.22 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid hydrazide from step b were suspended in 15 ml of DMF together with 1.43 g (6.22 mmol) of 1-Boc-piperazine-4-carboxylic acid (preparation analogous to Bioorganic & Medicinal Chemistry Letters, 2001, vol. 11, #24 p. 3161-3164), 2.41 g (12.45 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 867 mg (6.22 mmol) of 1-hydroxybenzotriazole hydrate. 1.40 ml (12.45 mmol) of 4-methylmorpholine were added to the reaction mixture, which was then stirred at room temperature overnight, stirred into 350 ml of water. The resultant precipitate was filtered off with suction, dissolved in DCM, dried, stripped off to dryness and purified by means of flash chromatography on silica gel.

Aufarbeitung

  1. filtrationThe resultant precipitate was filtered off with suction
  2. dissolutiondissolved in DCM
  3. customdried
  4. custompurified by means of flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3aa2aad101ef4d2a87f114ba358e0575
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08907098B2

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