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Sodium Hydroxide → {4-[({[(4-Tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetic acid

HRID 551898
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HRID 551898 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]([CH2:34][C:35]2[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41]([O:43]C)=[O:42])=[CH:37][CH:36]=2)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([N:14]([CH2:34][C:35]2[CH:46]=[CH:45][C:38]([O:39][CH2:40][C:41]([OH:43])=[O:42])=[CH:37][CH:36]=2)[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH3:33])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)=[O:13])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 11541808Methyl {4-[({[(4-tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetate

생성물 1

HCID 11570731{4-[({[(4-Tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetic acid수율 69.4%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of methyl {4-[({[(4-tert-butylphenyl)amino]carbonyl}{4-[(4-butylphenyl)-ethynyl]benzyl}amino)methyl]phenoxy}acetate (70 mg, 0.11 mmol) in MeOH (1 mL) and THF (1 mL) was added an aqueous solution of NaOH (0.5 mL, 5N) and the resulting mixture was stirred at it for 3 hrs. Then the solvents were removed under reduced pressure. The residue was taken up in EtOAc and washed with an aqueous solution of HCl (1N) and brine. The organic layer was dried over MgSO4 and the solvent was removed to give 46 mg (67%) of the title compound. HPLC, Rt: 5.67 min (purity: 97.4%). 1H NMR (CD3OD) δ: 7.48 (d, J=8.3 Hz, 2H), 7.40 (d, J=7.5 Hz, 2H), 7.18-7.33 (m, 10H), 6.93 (d, J=8.7 Hz, 2H), 4.66 (s, 2H), 4.66 (s, 2H), 4.54 (s, 2H), 2.63 (t, J=7.5 Hz, 2H), 1.60 (m, 2H), 1.37 (m, 2H), 1.30 (s, 9H), 0.95 (t, J=7.2 Hz, 3H). M+(ESI): 603.4, M−(ESI): 601.3.

후처리

  1. customThen the solvents were removed under reduced pressure
  2. washwashed with an aqueous solution of HCl (1N) and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed

출처 및 근거

ORD 기록
ord-95e5c3c844064223899c609bc434c392
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07947851B2

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