Hydrochloric Acid → Ethyl[5-(2-bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]-acetate

HRID 1444824

Reaktionsgleichung

Reaktionsgleichung von HRID 1444824
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][C:10]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:9]=2[CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Br:25])[CH2:7]1)[CH3:2].[C:27](N=P(N=P(N(C)C)(N(C)C)N(C)C)(N=P(N(C)C)(N(C)C)N(C)C)N=P(N(C)C)(N(C)C)N(C)C)([CH3:30])([CH3:29])[CH3:28].CCCCCC.ICC(C)C.Cl>C1COCC1.O>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][N:6]1[CH2:7][CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Br:25])[C:9]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=2[CH:11]([CH2:28][CH:27]([CH3:30])[CH3:29])[C:12]1=[O:13])[CH3:2]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 10556Isobutyl iodideHCID 4339838N'''-(1,1-Dimethylethyl)-N,N',N''-tris(tris(dimethylamino)phosphoranylidene)phosphorimidic triamideHCID 59025541Ethyl[1-(2-bromophenyl)-8-chloro-4-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]acetate

Produkt 1

HCID 59025471Ethyl[5-(2-bromophenyl)-7-chloro-1-isobutyl-2-oxo-1,2,4,5-tetrahydrobenzo[d]azepin-3-yl]-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

440 mg of the compound from Example 12A (1.01 mol) are dissolved in 5.2 ml of THF. At −78° C., 1.51 ml of a 1 M solution of 3-tert-butylimino-1,1,1,5,5,5-hexakis(dimethylamino)-3-[tris(dimethylamino)phosphoranylidene]amino-1λ5,3λ5,5λ5-1,4-triphosphazadiene in n-hexane (1.51 mol) are added drop wise, and the reaction mixture is stirred at −78° C. for 30 min. 278 mg of 1-iodo-2-methylpropane (1.51 mol) are added drop wise, and the mixture is stirred at −78° C. for a further 3 h. The reaction solution is mixed with 14 ml of 1 N hydrochloric acid and water and extracted three times with dichloromethane. The combined organic phases are washed twice with saturated sodium bicarbonate solution, dried over sodium sulphate and concentrated in a rotary evaporator. The residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 200 mg (40% of theory) of the title compound are obtained.

Aufarbeitung

  1. stirringthe mixture is stirred at −78° C. for a further 3 h
  2. extractionextracted three times with dichloromethane
  3. washThe combined organic phases are washed twice with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in a rotary evaporator
  6. customThe residue is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Quellen und Nachweise

ORD-Eintrag
ord-157706b8a6d248ec8dde787b21668192
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662956B2

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