Sodium Hydroxide → 6-Chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzoic acid

HRID 1469799Notes

Reaction equation

HRID 1469799 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:21])([CH3:20])[CH2:18][F:19])=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[C:5]([CH2:14][NH:15][C:16](=[O:22])[C:17]([CH3:20])([CH3:21])[CH2:18][F:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692272HCID 86692272, compound

Product 1

HCID 866922736-Chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzoic acidYield 91.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The title compound was prepared following the procedure described in step-3 of Intermediate-2 using ethyl 6-chloro-2-fluoro-3-((3-fluoro-2,2-dimethylpropanamido)methyl)benzoate (100 mg, 0.30 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) and NaOH (24 mg, 0.60 mmol) to afford 84 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.30 (t, 1H), 7.39-7.29 (m, 2H), 4.47-4.28 (m, 4H), 1.14 (s, 6H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-869ab567d9204e8eae304f383efa6519
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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