Sodium Hydroxide → HCID 14836068, compound

HRID 1088547Notes

Reaction equation

HRID 1088547 reaction equation
[OH-].[Na+].[CH2:3]([O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:22][CH3:23])[C:14]=2[C:18]([F:21])([F:20])[F:19])[C:9]=1[C:24]([N:26]([CH3:32])[CH2:27][C:28]([O:30]C)=[O:29])=[O:25])[CH2:4][CH2:5][CH3:6]>C1COCC1.CO>[CH2:3]([O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:22][CH3:23])[C:14]=2[C:18]([F:21])([F:20])[F:19])[C:9]=1[C:24]([N:26]([CH3:32])[CH2:27][C:28]([OH:30])=[O:29])=[O:25])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14836067HCID 14836067, compound

Product 1

HCID 14836068HCID 14836068, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (2.5N, 2.7 mL, 1.2 eq) was added to a stirred solution of N-[[2-butoxy-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]-N-methylglycine, methyl ester (2.35 g, 5.50 mmol) in THF (22 mL) and methanol (6 mL) at room temperature. After 11/2 hours the organic solvents were removed and the residue was taken up in water (250 mL). The aqueous phase was acidified to pH 1 with 10% HCl, then extracted with ethyl acetate. The extracts were combined, dried over MgSO4, and concentrated to give a solid which was triturated with petroleum ether to provide the title compound as a white solid (1.57 g, 69%), m.p. 152°-155° C.

Workup

  1. customAfter 11/2 hours the organic solvents were removed
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with petroleum ether

Sources & evidence

ORD record
ord-2dd6fc59fe724de496db7a40fa822d02
Source dataset
uspto-grants-1990_10
Patent number
US04962224

Reaction notes

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