Sodium Hydroxide → HCID 68890341, compound

HRID 1820996Notes

Reaction equation

HRID 1820996 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:18][C:17]=3[CH3:28])[O:13][N:12]=2)=[CH:7][C:6]=1[C:29]([F:32])([F:31])[F:30])([CH3:3])[CH3:2].[OH-].[Na+]>CCO>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:18][C:17]=3[CH3:28])[O:13][N:12]=2)=[CH:7][C:6]=1[C:29]([F:30])([F:31])[F:32])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68890408HCID 68890408, compound

Product 1

HCID 68890341HCID 68890341, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 33 mg (0.07 mmol) of methyl 3-(4-(3-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-5-yl)-3-methylphenyl)propanoate (from Step D) in 2.0 mL of EtOH was added 200 μL (1.0 mmol) of 5.0 N NaOH. The mixture was stirred at rt overnight. Purification by HPLC B gave 22 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.40 (d, J=6.0, 6H), 2.66 (t, J=7.7, 2H), 2.74 (s, 3H), 2.99 (t, J=7.6, 2H), 4.87 (m, 1H), 7.28-7.37 (m, 3H), 8.06 (d, J=8.0, 1H), 8.30-8.31 (m, 2H).

Workup

  1. customPurification by HPLC B

Sources & evidence

ORD record
ord-306b6c8da19d4ebd86d2abe37a95f502
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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