Water → Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1950353Notes

Reaction equation

HRID 1950353 reaction equation
C([O:4][C:5]1[CH:41]=[CH:40][C:8]([C:9]([N:11]([CH:37]([CH3:39])[CH3:38])[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[CH:20]2[CH2:29][CH2:28][C:27]3[CH:26]=[C:25]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH:24]=[CH:23][C:22]=3[CH2:21]2)=[O:10])=[CH:7][C:6]=1[F:42])(=O)C.O.C(=O)([O-])[O-].[K+].[K+]>CO>[F:42][C:6]1[CH:7]=[C:8]([CH:40]=[CH:41][C:5]=1[OH:4])[C:9]([N:11]([CH:37]([CH3:39])[CH3:38])[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[CH:20]1[CH2:29][CH2:28][C:27]2[CH:26]=[C:25]([O:30][C:31](=[O:36])[C:32]([CH3:33])([CH3:34])[CH3:35])[CH:24]=[CH:23][C:22]=2[CH2:21]1)=[O:10]

Participants

5

Reactant 3

HCID 962Water2×HCID 11430Potassium CarbonateHCID 57934107Pivalic acid 6-{2-[(4-acetoxy-3-fluorobenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934527Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterYield 62.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of pivalic acid 6-{2-[(4-acetoxy-3-fluorobenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (1.1 g) in methanol (18 ml) were sequentially added water (2 ml) and potassium carbonate (321 mg), and the solution was stirred for 1 hour at room temperature. Water was added thereto, the solution was extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (637 mg).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-4f1acac5c6a94bc796740521101615bb
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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