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Ammonia → (R)-2-(4-(9-Hydroxy-2-(3-hydroxy-3-methylbutoxy)-9-(trifluoromethyl)-9H-fluoren-4-yl)-1H-pyrazol-1-yl)-2-methylpropanamide

HRID 579389
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HRID 579389 반응식
[OH:1][C@@:2]1([C:33]([F:36])([F:35])[F:34])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[CH:11]=[C:10]([C:22]3[CH:23]=[N:24][N:25]([C:27]([CH3:32])([CH3:31])[C:28]([OH:30])=O)[CH:26]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.O[N:38]1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.N.Cl>CN(C)C=O.O>[OH:1][C@@:2]1([C:33]([F:35])([F:34])[F:36])[C:14]2[CH:13]=[C:12]([O:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[CH:11]=[C:10]([C:22]3[CH:23]=[N:24][N:25]([C:27]([CH3:32])([CH3:31])[C:28]([NH2:38])=[O:30])[CH:26]=3)[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2
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참가 물질

8

반응물 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1175992732-{4-[(9R)-9-Hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionic acid

생성물 1

HCID 78210288
(R)-2-(4-(9-Hydroxy-2-(3-hydroxy-3-methylbutoxy)-9-(trifluoromethyl)-9H-fluoren-4-yl)-1H-pyrazol-1-yl)-2-methylpropanamide
수율 90.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Under a nitrogen atmosphere, 2-{4-[(9R)-9-hydroxy-2-(3-hydroxy-3-methylbutyloxy)-9-(trifluoromethyl)-9H-fluoren-4-yl]-1H-pyrazol-1-yl}-2-methylpropionic acid (66.7 g) was dissolved in N,N-dimethylformamide (480 ml), 1-hydroxybenzotriazole (HOBt) 1 hydrate (27.6 g), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (WSC) hydrochloride (34.6 g) and 28% aqueous ammonia (24.5 ml) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was ice-cooled, water (630 ml) and 2N hydrochloric acid (330 ml) were added dropwise, and the mixture was extracted with ethyl acetate (800 ml). The obtained aqueous layer was extracted again with ethyl acetate (500 ml). The obtained organic layers were combined, and washed successively with water (500 ml, twice), saturated aqueous sodium hydrogen carbonate (500 ml), and saturated brine (500 ml). The obtained organic layer was dried over anhydrous sodium sulfate, the insoluble material was filtered off, and the solvent in the filtrate was evaporated to give the title compound (60.0 g).

후처리

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate (800 ml)
  3. extractionThe obtained aqueous layer was extracted again with ethyl acetate (500 ml)
  4. washwashed successively with water (500 ml
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. filtrationthe insoluble material was filtered off
  7. customthe solvent in the filtrate was evaporated

출처 및 근거

ORD 기록
ord-07780a5e12444189ad899a1d1986db08
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040717B2

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