Sodium Hydroxide → HCID 12114188, compound

HRID 432926Notes

Reaction equation

HRID 432926 reaction equation
C[O:2][C:3](=[O:35])[CH:4]([CH3:34])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:17]=2)=[C:10]([CH3:33])[CH:9]=1)=[O:6].[OH-].[Na+]>O.CO.CCOC(C)=O>[F:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[OH:22])[O:15][C:11]2[C:12]([CH3:14])=[CH:13][C:8]([NH:7][C:5](=[O:6])[CH:4]([CH3:34])[C:3]([OH:35])=[O:2])=[CH:9][C:10]=2[CH3:33])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10028970HCID 10028970, compound

Product 1

HCID 12114188HCID 12114188, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of N-{4-[3-(4-Fluoro-benzenesulfonyl)-4-hydroxy-phenoxy]-3,5-dimethyl-phenyl}-2-methyl-malonamic acid methyl ester (155 mg, 0.31 mmol) in H2O/MeOH (1/1, 4 mL) was added 1N NaOH (0.6 mL, 0.6 mmol). After stirring at room temperature for 1 h, the solution was diluted with EtOAc (15 mL) and extracted with 0.1 N NaOH (3×10 mL). The combined basic extracts were acidified with 1M HCl and extracted with EtOAc (3×15 mL). The organic extracts were combined, washed with brine, dried and concentrated to give the title compound of Step B and Example 4-4 (131 mg) as a solid. 1H NMR (400 MHz, CD3OD) δ 7.98-7.95 (m, 2H), 7.35 (s, 2H), 7.27-7.22 (m, 3H), 6.93-6.90 (dd, 1H), 6.80 (d, 1H), 3.57-3.52 (q, 1H), 2.05 (s, 6H), 1.41 (d, 3H). MS (ES31) Calc: 487.1, Found: 485.9 (M−1).

Workup

  1. extractionextracted with 0.1 N NaOH (3×10 mL)
  2. extractionextracted with EtOAc (3×15 mL)
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4bb0e2a8159440348f3d0b9ee7cc60c8
Source dataset
uspto-grants-2003_12
Patent number
US06664291B2

Reaction notes

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