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

HRID 646027Notes

Reaction equation

HRID 646027 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:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]=[C:29]([C:34]([O:36]C)=[O:35])[CH:28]=[CH:27]4)=[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:19]=[CH:20][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[CH:30]=[C:29]([C:34]([OH:36])=[O:35])[CH:28]=[CH:27]4)=[CH:22][CH:23]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24739328Methyl 6-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate

Product 1

HCID 592648606-[4-({[3-[2-(2,6-Dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 6-[4-({[3-[2-(2,6-dichlorophenyl)ethyl]-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-naphthalenecarboxylate (0.035 g, 0.061 mmol) in tetrahydrofuran (0.6 mL) was placed in a microwave reaction tube. Methanol (0.3 mL) was added followed by 1N sodium hydroxide (0.092 mL, 0.092 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 (0.027 g, 77.1%) 1H NMR (DMSO-d6): δ 13.03 (s, 1H), 8.58 (s, 1H), 8.24 (s, 1H), 8.15 (d, J=9 Hz, 1H), 8.03 (d, J=9 Hz, 1H), 7.96 (dd, J=2, 9 Hz, 1H), 7.90 (dd, J=2, 9 Hz, 1H), 7.81 (d, J=9, 2H), 7.42 (d, J=8 Hz, 2H), 7.25 (m, 1H), 7.14 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.35 (septet, J=7 Hz, overlapping H2O, 1H), 3.24-3.20 (m, 2H), 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-37be44e9c0f042dba75d31994d9bbdbb
Source dataset
uspto-grants-2010_04
Patent number
US07705028B2

Reaction notes

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