Sodium Hydroxide → HCID 23157438, compound

HRID 508088Notes

Reaction equation

HRID 508088 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH:18]3[CH3:27])=[C:12]([O:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:33][CH2:34][C:35]([O:37]CC)=[O:36].[OH-].[Na+].C(=O)([O-])O.[Na+]>CO.O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20][CH2:19][CH:18]3[CH3:27])=[C:12]([O:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:33][CH2:34][C:35]([OH:37])=[O:36]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23157493HCID 23157493, compound

Product 1

HCID 23157438HCID 23157438, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-[2-fluoro-4-({4-[(2-methyl-3,4-dihydroquinolin-1(2H)-yl)methyl]-3-[(methylsulfonyl)oxy]benzyl}amino)phenyl]propanoate (0.60 g, 1.07 mmol) in a mixture of methanol (3.0 mL) and tetrahydrofuran (6.0 mL) was added 1 N aqueous sodium hydroxide solution (2.14 mL, 2.14 mmol), and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with 10% aqueous citric acid solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by preparative HPLC (gradient cycle A) to give a colorless oil. The obtained oil was dissolved in ethyl acetate, and the solution was neutralized with saturated aqueous sodium hydrogencarbonate solution, washed with saturated brine and dried to give the title compound (0.25 g, yield 56%) as a colorless oil.

Workup

  1. washthe organic layer was washed with 10% aqueous citric acid solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC (gradient cycle A)
  5. customto give a colorless oil
  6. washwashed with saturated brine
  7. customdried

Sources & evidence

ORD record
ord-24cf7c2351224af59cc4b908c6d9107b
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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