Hydrochloric Acid → 7-[4-({[3-{[(2,6-Dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylic acid

HRID 2423451ノート

反応式

HRID 2423451 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:33]=[C:32]4[C:27]([CH:28]=[C:29]([C:34]([O:36]C)=[O:35])[N:30]=[CH:31]4)=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:33]=[C:32]4[C:27]([CH:28]=[C:29]([C:34]([OH:36])=[O:35])[N:30]=[CH:31]4)=[CH:26][CH:25]=3)=[CH:22][CH:23]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321481Methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate

生成物 1

HCID 593214727-[4-({[3-{[(2,6-Dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylic acid収率 75%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To a solution of methyl 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylate (44 mg, 0.082 mmol) in 2:1 tetrahydrofuran:methanol (3 mL) was added 0.123 mL of 1 N sodium hydroxide. The solution was heated in a microwave reactor at 100° C. for 500 seconds. Then 1N hydrochloric acid (0.123 mL, 0.123 mmol) was added and the solution was concentrated. The residue was taken up with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combine organic layers were washed with brine, dried over magnesium sulfate and concentrated. The resulting solid was dried under vacuum overnight and then suspended in ethyl acetate and washed three times with water. The solvent was evaporated to afford 7-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-isoquinolinecarboxylic acid (32 mg, 75%). 1H-NMR (400 MHz, DMSO-d6) δ 9.41 (s, 1H), 8.61 (s, 1H), 8.50 (s, 1H), 8.24-8.19 (m, 2H), 7.86 (d, J=9 Hz, 2H), 7.19 (d, J=9 Hz, 2H), 7.00-6.91 (m, 3H), 5.09 (s, 2H), 4.90 (s, 2H), 3.41 (septet, J=7 Hz, 1H), 2.14 (s, 6H), 1.27 (d, J=7 Hz, 6H). HRMS (ESI) C32H30N2O5 calculated: 523.2228 (M+H)+, found: 523.2230 (M+H)+.

後処理

  1. concentrationthe solution was concentrated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combine organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting solid was dried under vacuum overnight
  7. washwashed three times with water
  8. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-d589a5e7dcb24045aa9e29566bbd9651
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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