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Lithium hydroxide, monohydrate → HCID 86700858, 화합물

HRID 881753
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HRID 881753 반응식
C[O:2][C:3](=[O:35])[CH2:4][C:5]12[CH2:12][CH2:11][C:8]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]5[O:27][C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])=[N:29][N:30]=5)=[CH:21][CH:20]=4)=[CH:15][CH:14]=3)([CH2:9][CH2:10]1)[O:7][CH2:6]2.O.[OH-].[Li+]>O1CCCC1.C(O)C.O>[C:31]([C:28]1[O:27][C:26]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([C:8]45[CH2:9][CH2:10][C:5]([CH2:4][C:3]([OH:35])=[O:2])([CH2:12][CH2:11]4)[CH2:6][O:7]5)=[CH:14][CH:15]=3)=[CH:24][CH:23]=2)=[N:30][N:29]=1)([CH3:34])([CH3:32])[CH3:33]
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참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86700856HCID 86700856, 화합물

생성물 1

HCID 86700858HCID 86700858, 화합물수율 71.6%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A 100 ml round bottom flask was charged with {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid methyl ester (0.27 g, 0.454 mmol), and lithium hydroxide monohydrate (0.229 g, 5.45 mmol) in tetrahydrofuran (20 ml), ethanol (10 ml) and water (8 ml) at room temperature. The mixture was heated at 50° C. for 2 hours. Most of the organic solvent was evaporated under vacuum and the mixture was acidified to PH=4 at 0° C. The solvents were then removed by lipherlizer. The mixture was added ethanol (40 ml) and heated to 70° C., and then was cooled to room temperature. The mixture was filtered and the solid was washed with ethanol (3 ml) and water (10 ml) to afford {1-[4′-(5-tert-butyl-[1,3,4]oxadiazol-2-ylamino)-biphenyl-4-yl]-2-oxa-bicyclo[2.2.2]oct-4-yl}-acetic acid (150 mg, 71%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.89 (m, 6H) 2.00-2.13 (m, 4H) 3.85 (s, 2H) 7.42 (d, J=8.40 Hz, 2H) 7.55 (d, J=8.50 Hz, 2H) 7.62 (s, 4H) 10.46 (br. s, 1H). LC/MS, [MS+] 461.23, RT: 2.66 (Condition M).

후처리

  1. customMost of the organic solvent was evaporated under vacuum
  2. customat 0° C
  3. customThe solvents were then removed by lipherlizer
  4. additionThe mixture was added ethanol (40 ml)
  5. temperatureheated to 70° C.
  6. temperaturewas cooled to room temperature
  7. filtrationThe mixture was filtered
  8. washthe solid was washed with ethanol (3 ml) and water (10 ml)

출처 및 근거

ORD 기록
ord-9f44fda6f32e4dd18d62bf412400513b
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08993619B2

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