Hydrochloric Acid → 4'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid

HRID 1845265노트

반응식

HRID 1845265 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([O:23]C)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:11]=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58188218Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

생성물 1

HCID 581880344'-Methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 4′-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate (60 mg, 0.19 mmol) in tetrahydrofuran (3 mL) was added 2.5 M aqueous lithium hydroxide solution (0.77 mL, 1.9 mmol). The mixture was stirred at room temperature overnight, and then acidified to pH=5 by addition of 2N aqueous HCl and extracted with EtOAc (50 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford the title product. 1H NMR (CD3OD, 400 MHz): 8.63 (d, 2H, J=4.8 Hz), 8.16 (t, 1H, J=1.6 Hz), 7.74 (t, 1H, J=2.0 Hz), 7.65 (t, 1H, J=2.0 Hz), 7.56 (d, 2H, J=8.0 Hz), 7.29 (d, 2H, J=8.0 Hz), 7.24 (t, 1H, J=4.8 Hz), 2.39 (s, 3H).

후처리

  1. extractionextracted with EtOAc (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c2fcbbe10527462fa13b388eb2201d56
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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