Hydrochloric Acid → Ethyl[7-chloro-1-isobutyl-5-(2-methoxyphenyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-acetate

HRID 1444829

반응식

HRID 1444829 반응식
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[C:10]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:9]=2[CH2:8][C:7]1=[O:26])[CH3:2].[C:28](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)([CH3:31])([CH3:30])[CH3:29].ICC(C)C.Cl>C1COCC1.CCCCCC.O>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:7](=[O:26])[CH:8]([CH2:29][CH:28]([CH3:31])[CH3:30])[C:9]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:10]=2[CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH2:12]1)[CH3:2]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10556Isobutyl iodideHCID 4339838N'''-(1,1-Dimethylethyl)-N,N',N''-tris(tris(dimethylamino)phosphoranylidene)phosphorimidic triamideHCID 59025538Ethyl[8-chloro-1-(2-methoxyphenyl)-4-oxo-1,2,4,5-tetrahydro-3h-3-benzazepin-3-yl]acetate

생성물 1

HCID 59025486Ethyl[7-chloro-1-isobutyl-5-(2-methoxyphenyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]-acetate

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

134 mg of the compound from Example 22A (0.35 mol) are dissolved in 1.35 ml of THF. At −78° C., 0.52 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 (P4-t-Bu; 328 mg, 0.52 mol) in n-hexane is added drop wise, and the reaction solution is stirred at −78° C. for 30 min. 191 mg of 1-iodo-2-methylpropane (1.04 mol) are added drop wise, and the mixture is stirred at −78° C. for a further 2 h. The reaction solution is mixed with 10 ml of 1 N hydrochloric acid and water and extracted three times with dichloromethane. The combined organic phases are washed 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, gradient 20:80→95:5). 87 mg (57% of theory) of the title compound are obtained.

후처리

  1. stirringthe mixture is stirred at −78° C. for a further 2 h
  2. extractionextracted three times with dichloromethane
  3. washThe combined organic phases are washed 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, gradient 20:80→95:5)

출처 및 근거

ORD 기록
ord-bcb4db5ef2354af6bee46983114a913e
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662956B2

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