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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium hydride → 2''-({5-[3,5-Bis(trifluoromethyl)phenyl]-4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylic acid

HRID 2093228
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HRID 2093228 반응식
C(O[C:9](=[O:30])[NH:10][C:11]([CH3:29])([CH3:28])[CH:12]([C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)[OH:13])C1C=CC=CC=1.[H-].[Na+].Br[CH2:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:36]=1[C:45]1[CH:46]=[C:47]([C:53]2[CH:58]=[CH:57][C:56]([C:59]([O:61]C)=[O:60])=[CH:55][C:54]=2[CH3:63])[CH:48]=[CH:49][C:50]=1[O:51][CH3:52]>C1COCC1>[F:26][C:24]([F:25])([F:27])[C:16]1[CH:15]=[C:14]([CH:12]2[O:13][C:9](=[O:30])[N:10]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:36]=3[C:45]3[CH:46]=[C:47]([C:53]4[CH:58]=[CH:57][C:56]([C:59]([OH:61])=[O:60])=[CH:55][C:54]=4[CH3:63])[CH:48]=[CH:49][C:50]=3[O:51][CH3:52])[C:11]2([CH3:29])[CH3:28])[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydride2회HCID 53363830Benzyl {2-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-1,1-dimethylethyl}carbamateHCID 57544358Methyl 2''-(bromomethyl)-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

생성물 1

HCID 250098732''-({5-[3,5-Bis(trifluoromethyl)phenyl]-4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of benzyl{2-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-1,1-dimethylethyl}carbamate (65 mg, 0.149 mmol) in THF (1.5 mL) was added NaH (13 mg, 0.542 mmol) and methyl 2″-(bromomethyl)-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (91.1 mg, 0.185 mmol). The reaction was stirred for 72 hours, and then additional NaH (36.2 mg, 1.51 mmol) was added. After 6 more hours at room temperature, the reaction was quenched with saturated NH4C1 solution (10 mL) and diluted with EtOAc (20 mL). The aqueous layer was extracted with EtOAc (20 mL), and the combined organic extracts were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. Purification of the residue by reverse-phase chromatography (C-18, 10 to 95% MeCN/water with 0.1% TFA) afforded 2″-({5-[3,5-bis(trifluoromethyl)phenyl]-4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS=726.0 (M+1)+. 1H NMR (CDCl3, 500 MHz, rotamers present) δ 8.03-8.02 (m, 1H), 7.80-7.96 (m, 1H), 7.89 (s, 1H), 7.79-7.76 (m, 2H), 7.62-7.59 (m, 1H), 7.42-7.31 (m, 3H), 7.22-7.08 (m, 3H), 5.26-5.28 (m, 1H), 4.81 (d, J=16.6 Hz), 4.44-4.42 (m, 1H), 4.02 (d, J=16.6 Hz), 3.85 (s, 3H), 2.37-2.35 (m, 3H), 1.24 (s), 10.6 (s), 0.56-0.54 (m, 3H).

후처리

  1. customAfter 6 more hours at room temperature, the reaction was quenched with saturated NH4C1 solution (10 mL)
  2. additiondiluted with EtOAc (20 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (20 mL)
  4. washthe combined organic extracts were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by reverse-phase chromatography (C-18, 10 to 95% MeCN/water with 0.1% TFA)

출처 및 근거

ORD 기록
ord-32e55ff9430d4ed8b70351e3ddc83eae
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08440702B2

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