1-Hydroxybenzotriazole → tert-butyl (2R)-2-[(cyclopropyl{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}amino)carbonyl]morpholine-4-carboxylate

HRID 922417노트

반응식

HRID 922417 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:12]2[CH:13]=[CH:14][O:15][C:11]=2[CH:10]=[C:9]([CH:16]([NH:18][CH:19]2[CH2:21][CH2:20]2)[CH3:17])[CH:8]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][O:32][C@@H:31]([C:35](O)=[O:36])[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:19]1([N:18]([CH:16]([C:9]2[CH:8]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]3[CH:13]=[CH:14][O:15][C:11]=3[CH:10]=2)[CH3:17])[C:35]([C@@H:31]2[O:32][CH2:33][CH2:34][N:29]([C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:30]2)=[O:36])[CH2:20][CH2:21]1

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6559076(2R)-4-((tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 68309919HCID 68309919, 화합물

생성물 1

HCID 68309685tert-butyl (2R)-2-[(cyclopropyl{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}amino)carbonyl]morpholine-4-carboxylate수율 88.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}-cyclopropanamine (200 mg) and (2R)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (240 mg) in N,N-dimethylformamide (7 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (212 mg) and 1-hydroxybenzotriazole (140 mg) under ice-cooling, and then stirred at room temperature for 18 hours. To the reaction mixture was added aqueous saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with water, 10% aqueous citric acid solution and saturated saline, and then concentrated under reduced pressure to give tert-butyl (2R)-2-[(cyclopropyl{1-[4-(3-methoxypropoxy)-1-benzofuran-6-yl]ethyl}amino)carbonyl]morpholine-4-carboxylate [Ex(161-1)] (306 mg) as a yellow oil.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water, 10% aqueous citric acid solution and saturated saline
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4c570cddb6554540bf1d77a1f4f22a21
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278944B2

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