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Hydrochloric Acid → (2S)-2-tert-butoxy-2-[5-[4-[2-(4-fluorophenyl)ethoxy]phenyl]-4-(4-methoxy-4-methyl-1-piperidyl)-2,6-dimethyl-3-pyridyl]acetic acid

HRID 718469
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HRID 718469 반응식
[OH-].[K+].[C:3]([O:7][C@@H:8]([C:15]1[C:16]([CH3:47])=[N:17][C:18]([CH3:46])=[C:19]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:32][CH:31]=2)[C:20]=1[N:21]1[CH2:26][CH2:25][C:24]([O:28][CH3:29])([CH3:27])[CH2:23][CH2:22]1)[C:9]([O:11]C(C)C)=[O:10])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C>[C:3]([O:7][C@@H:8]([C:15]1[C:16]([CH3:47])=[N:17][C:18]([CH3:46])=[C:19]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:34][CH:35]=2)[C:20]=1[N:21]1[CH2:22][CH2:23][C:24]([O:28][CH3:29])([CH3:27])[CH2:25][CH2:26]1)[C:9]([OH:11])=[O:10])([CH3:6])([CH3:5])[CH3:4]
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HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 118307837(S)-isopropyl 2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate

생성물 1

HCID 118307680(2S)-2-tert-butoxy-2-[5-[4-[2-(4-fluorophenyl)ethoxy]phenyl]-4-(4-methoxy-4-methyl-1-piperidyl)-2,6-dimethyl-3-pyridyl]acetic acid수율 21.5%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

The potassium hydroxide (230 mg, 4.1 mmol) was added to a gave (S)-isopropyl 2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetate (255 mg, 0.41 mmol) in ethanol (4 mL) and stirred for 6 h at 90° C. The reaction mixture was neutralized with 1N HCl solution, extracted with EtOAc, and the organic layer was washed with brine, and dried (MgSO4). The crude material was purified by prep to give (S)-2-(tert-butoxy)-2-(5-(4-(4-fluorophenethoxy)phenyl)-4-(4-methoxy-4-methylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)acetic acid 51 mg (21%) as a mixture of diastereomers. 1H NMR (500 MHz, DMSO-d6) δ 7.39-7.36 (m, 2H), 7.19-7.12 (m, 3H), 7.02-6.99 (m, 3H), 5.81 (s, 1H), 4.24-4.21 (m, 2H), 3.49 (br. s, 4H), 3.07-3.04 (m, 2H), 2.89/2.81 (s, 3H), 2.44 (s, 3H), 2.04 (s, 3H), 1.59-1.45 (m, 3H), 1.32-1.25 (m, 1H), 1.12 (br. s, 9H), 0.99/0.81 (s, 3H). UPLC (M+H)=579.5.

후처리

  1. extractionextracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customThe crude material was purified by prep

출처 및 근거

ORD 기록
ord-80cdfc961b8f4c8e8e8ea1515b2e8d96
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09193720B2

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