1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (-)-1-(9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carbonyl)-azetidine-3-carboxylic acid dimethylamide

HRID 541147노트

반응식

HRID 541147 반응식
[OH:1][C:2]1([C:19]([F:22])([F:21])[F:20])[C:14]2[CH:13]=[C:12]([C:15]([OH:17])=O)[CH:11]=[C:10]([CH3:18])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.Cl.[CH3:24][N:25]([CH3:32])[C:26]([CH:28]1[CH2:31][NH:30][CH2:29]1)=[O:27].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH3:24][N:25]([CH3:32])[C:26]([CH:28]1[CH2:31][N:30]([C:15]([C:12]2[CH:11]=[C:10]([CH3:18])[C:9]3[C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2]([OH:1])([C:19]([F:20])([F:21])[F:22])[C:14]=3[CH:13]=2)=[O:17])[CH2:29]1)=[O:27]

참가 물질

8

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53308702N,N-dimethylazetidine-3-carboxamide hydrochlorideHCID 594925279-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylic acid

생성물 1

HCID 59493074(-)-1-(9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carbonyl)-azetidine-3-carboxylic acid dimethylamide수율 50%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of an optically active form (0.080 g) of 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylic acid, azetidine-3-carboxylic acid dimethylamide hydrochloride (0.060 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.065 g), 1-hydroxybenzotriazole hydrate (0.052 g) and dimethylformamide (2 ml) was added triethylamine (0.073 ml), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added ethyl acetate (15 ml), and the mixture was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and 3 times with water. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was treated with ethyl ether. This slurry was filtered and the obtained solid was dried to give the title compound (0.054 g, 50%).

후처리

  1. washthe mixture was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and 3 times with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionthe obtained residue was treated with ethyl ether
  6. filtrationThis slurry was filtered
  7. customthe obtained solid was dried

출처 및 근거

ORD 기록
ord-b877d73070224a9a832afa4580269999
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871934B2

반응 노트

불러오는 중…