Sodium Hydroxide → 2-Chloro-4-fluoro-3-(pivalamidomethyl)benzoic acid

HRID 1469792Notes

Reaction equation

HRID 1469792 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:10]([F:20])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[C:11]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])=[C:10]([F:20])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692269Methyl 2-chloro-4-fluoro-3-(pivalamidomethyl)benzoate

Product 1

HCID 866922712-Chloro-4-fluoro-3-(pivalamidomethyl)benzoic acidYield 74.9%

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 methyl 2-chloro-4-fluoro-3-(pivalamidomethyl)benzoate (350 mg, 1.16 mmol) in THF:MeOH:H2O (3:2:1; 6 mL) and NaOH (93 mg, 2.32 mmol) to afford 250 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 12.55 (br s, 1H), 7.78 (m, 2H), 7.32-7.26 (t, J=8.7 Hz, 1H), 4.38 (d, J=4.5 Hz, 2H), 1.07 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-383549d0a2bc4337a53868874b6739ef
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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