Methanol → 7-[4-({[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylic acid

HRID 1693675Notes

Reaction equation

HRID 1693675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][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]=[CH:29][C:30]([C:34]([O:36]C)=[O:35])=[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.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][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]=[CH:29][C:30]([C:34]([OH:36])=[O:35])=[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

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59264866Methyl 7-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate

Product 1

HCID 247391727-[4-({[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylic acidYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 7-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate (0.057 g, 0.1 mmol) in tetrahydrofuran (1.0 mL) was placed in a microwave reaction tube. Methanol (0.5 mL) was added followed by 1 N sodium hydroxide (0.15 mL, 0.15 mmol). The tube was sealed and heated in a microwave reactor to 100° C. for 600 seconds. The solution was neutralized and concentrated. Water was added and the mixture was filtered. The resulting solid was dried in a vacuum oven at 45° C. with P2O5 to yield the title compound (0.048 g, 76% as 0.20 tetrahydrofuran) 1H NMR (DMSO-d6) 13.4-12.8 (broad s, approximately 1H), 8.59 (s, 1H), 8.31 (s, 1H), 8.01 (d, J=9 Hz, 1H) 7.94-7.90 (m, 3H), 7.79 (d, J=8 Hz, 2H), 7.43 (d, J=8 Hz, 2H), 7.28-7.24 (m, 1H), 7.14 (d, J=8 Hz, 2H), 4.98 (s, 2H), 3.39-3.21 (2m, overlapping H2O, total 3H), 2.89-2.85 (m, 2H), 1.25 (d, J=7 Hz, 6H). HRMS C32H27NO4Cl2 m/z 560.1395 (M+H)+Cal; 560.1409 (M+H)+Obs.

Workup

  1. customThe tube was sealed
  2. concentrationconcentrated
  3. additionWater was added
  4. filtrationthe mixture was filtered
  5. dry with materialThe resulting solid was dried in a vacuum oven at 45° C. with P2O5

Sources & evidence

ORD record
ord-086cd2bcc2fc4fb1a18d48a35d204499
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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