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

HRID 1693661노트

반응식

HRID 1693661 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2회HCID 59264872Ethyl 6-[4-({[3-[(2,6-dichlorophenyl)methyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-1-naphthalenecarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f60831415dea4f6bbe2957533dc05582
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158665B2

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