Sodium Hydroxide → HCID 68453838, compound

HRID 2358397Notes

Reaction equation

HRID 2358397 reaction equation
C([O:3][C:4](=[O:22])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])C.[OH-].[Na+]>CO.O>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH:6]=[CH:5][C:4]([OH:22])=[O:3])=[C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:9]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68456890HCID 68456890, compound

Product 1

HCID 68453838HCID 68453838, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-[4-tert-Butyl-2-(2-methoxyethoxy)phenyl]acrylic acid ethyl ester (40.4 mg, 0.132 mmol, 1 eq) and sodium hydroxide (52.8 mg, 1.32 mmole, 10 eq) were added in methanol and H2O. The reaction mixture was purified according to step 2 of Example 22 to give 3-[4-tert-Butyl-2-(2-methoxyethoxy)phenyl]acrylic acid (36.5 mg, 77.3%). 3-[4-tert-Butyl-2-(2-methoxyethoxy)-phenyl]acrylic acid (26.4 mg, 0.095 mmol, 1 eq.), Diethylcyanophosphine (17.3 μl, 0.114 mmol, 1.2 eq), N-(4-Aminomethyl-2-fluoro-6-vinylphenyl)methanesulfonamide (40.8 mg, 0.1114 mol, 1.2 eq.), and Triethylamine (39.7 μl, 0.285 mmol, 3 eq) were added in DMF. The mixture was stirred for overnight at room temperature. The reaction mixture was purified according to Example 17 to give a whitish solid (28.4 mg, 59.2%).

Workup

  1. customThe reaction mixture was purified

Sources & evidence

ORD record
ord-6129ba14773044749746fbf1471e86e1
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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