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

HRID 1693661ノート

反応式

HRID 1693661 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[C:29]([C:33]([O:35]CC)=[O:34])=[CH:28][CH:27]=[CH:26]4)=[CH:19][CH:18]=2)=[C:13]([CH:38]([CH3:40])[CH3:39])[O:12][N:11]=1.C(O)C.[OH-].[Na+].Cl>O1CCCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][C:10]1[C:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[C:29]([C:33]([OH:35])=[O:34])=[CH:28][CH:27]=[CH:26]4)=[CH:21][CH:22]=2)=[C:13]([CH:38]([CH3:40])[CH3:39])[O:12][N:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2 回HCID 59264872Ethyl 6-[4-({[3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate

生成物 1

HCID 247390196-[4-({[3-[(2,6-Dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylic acid収率 102.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A solution of ethyl 6-[4-({[3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate (0.116 g, 0.20 mmol) in tetrahydrofuran (2 mL) was placed in a microwave reaction tube. Ethanol (1 mL) was added followed by 1 N sodium hydroxide (0.312 mL, 0.31 mmol). The tube was sealed and heated in a microwave reactor to 100° C. for 500 seconds. Additional sodium hydroxide solution (0.2 mL, 0.2 mmol) was added and the solution was heated in a microwave reactor to 100° C. for another 500 seconds. The solution was neutralized with 1 N hydrochloric acid and concentrated. The residue was slurried in hexanes. The solid was slurried in water and the mixture was decanted and the solid dried to yield the title compound as a white solid (0.112 g, 100% as 0.15EtOAc). 1H NMR (DMSO-d6) 13.14 (s, 1H), 8.91 (d, J=9 Hz, 1H), 8.26 (s, 1H), 8.20 (d, J=8 Hz, 1H), 8.10 (d, J=7 Hz, 1H), 7.96 (dd, J=2, 9 Hz, 1H), 7.80 (d, J=9 Hz, 2H), 7.58 (m, 1H), 7.46 (d, J=8 Hz, 2H), 7.31 (t, J=8 Hz, 1H), 7.16 (d, J=9 Hz, 2H), 5.08 (s, 2H), 4.29 (s, 2H), 3.36 (septet, J=7 Hz, overlapping H2O 1H), 1.22 (d, J=7 Hz, 6H). HRMS C31H25NO4Cl2 m/z 546.1239 (M+H)+Cal; 546.1226 (M+H)+Obs.

後処理

  1. customThe tube was sealed
  2. temperaturethe solution was heated in a microwave reactor to 100° C. for another 500 seconds
  3. concentrationconcentrated
  4. customthe mixture was decanted
  5. customthe solid dried

出典と根拠

ORDレコード
ord-f60831415dea4f6bbe2957533dc05582
出典データセット
uspto-grants-2012_04
特許番号
US08158665B2

反応ノート

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