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Hydrochloric Acid → 5-((4-((4-Butylphenyl)ethynyl)benzyl)(hexyl)amino)-2-hydroxybenzoic acid

HRID 551891
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HRID 551891 반응식
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]3[CH:20]=[CH:21][C:22]([OH:29])=[C:23]([CH:28]=3)[C:24]([O:26]C)=[O:25])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:37]=[CH:36][C:16]([CH2:17][N:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:19]3[CH:20]=[CH:21][C:22]([OH:29])=[C:23]([CH:28]=3)[C:24]([OH:26])=[O:25])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11562363Methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate

생성물 1

HCID 114972825-((4-((4-Butylphenyl)ethynyl)benzyl)(hexyl)amino)-2-hydroxybenzoic acid

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

실험 절차

To a solution of methyl 5-[{4-[(4-butylphenyl)ethynyl]benzyl}(hexyl)amino]-2-hydroxybenzoate in MeOH (400 mL) and water (40 mL) was added an aqueous solution of NaOH (6.0 mL, 5N). The reaction mixture was sired at 60° C. overnight. Then an aqueous solution of HCl (10 mL, 5N) was added and the solvents were removed under reduced pressure. The residue was taken up in water and extracted with Et2O (3×). The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure to give a yellow solid. Precipitation from a DCM/MeOH mixture gave 2.17 g (53%, stop e and f) of the title compound as a beige powder. HPLC, Rt: 4.8 min purity: 99.7%). LC/MS, M+(ESI): 484.4, M−(ESI): 482.2. 1H NMR (CDCl3/CD3OD (15/1)) δ: 7.39 (m, 4H), 7.18-7.09 (m, 5H), 6.87 (dd, J=9.0, 3.0 Hz, 11), 6.78 (d, J=9.0 Hz, 1H), 4.38 (s, 2H), 3.22 (t, J=7.5 Hz, 2H), 2.57 (t, J=7.8 Hz, 2H), 1.55 (m, 4H), 1.34-1.21 (m, 8H), 0.90-0.75 (m, 6H).

후처리

  1. customthe solvents were removed under reduced pressure
  2. extractionextracted with Et2O (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. customto give a yellow solid
  6. customPrecipitation from a DCM/MeOH mixture

출처 및 근거

ORD 기록
ord-d4a88a61a5de431fb5357613fe1c6291
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947851B2

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