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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Acetic Acid → [(3R,4S)-3-[(R)-1-(5-Chloro-pyridin-2-yloxy)-2-hydroxy-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(2-methyl-pyrimidin-5-yl)-methanone

HRID 906938
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HRID 906938 반응식
C([Si](C)(C)[O:6][CH2:7][C@@H:8]([C@@H:17]1[C@@H:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:20][N:19]([C:30]([C:32]2[CH:37]=C(C)N=[N:34][CH:33]=2)=[O:31])[CH2:18]1)[O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1)(C)(C)C.C(O)(=O)C.CC[CH2:47][CH2:48][N+:49](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C@H:8]([C@@H:17]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH2:20][N:19]([C:30]([C:32]3[CH:33]=[N:34][C:48]([CH3:47])=[N:49][CH:37]=3)=[O:31])[CH2:18]2)[CH2:7][OH:6])=[N:11][CH:12]=1
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참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 67131632[(3R,4S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone

생성물 1

HCID 57576327[(3R,4S)-3-[(R)-1-(5-Chloro-pyridin-2-yloxy)-2-hydroxy-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(2-methyl-pyrimidin-5-yl)-methanone수율 91%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of [(3R,4S)-3-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(5-chloro-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-(6-methyl-pyridazin-4-yl)-methanone (0.074 g, 0.119 mmol) dissolved in THF (4 mL) was added 0.014 mL (0.24 mmol) of acetic acid and 0.119 mL of TBAF (1.0M in THF). The reaction mixture was stirred over night at room temperature. The mixture was diluted with ethyl acetate and washed with water and aq. sodium bicarbonate solution subsequently. The separated organic phase was dried over sodium sulfate and concentrated in vaccuo after filtration. The residue was purified by TLC (SiO2, MeOH/DCM, 1:10) yielded 55 mg (91%) of the title compound as a light yellow oil. ES-MS m/e: 507.1 (M+H+).

후처리

  1. washwashed with water and aq. sodium bicarbonate solution subsequently
  2. dry with materialThe separated organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vaccuo
  4. filtrationafter filtration
  5. customThe residue was purified by TLC (SiO2, MeOH/DCM, 1:10)

출처 및 근거

ORD 기록
ord-d67a27c5330c4d67a0c725c5d6708940
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012998B2

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