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

HRID 1469786Notes

Reaction equation

HRID 1469786 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][OH: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][OH:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86692262HCID 86692262, compound

Product 1

HCID 866922636-Chloro-2-fluoro-3-((3-hydroxy-2,2-dimethylpropanamido)methyl)benzoic acidYield 78.1%

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-hydroxy-2,2-dimethylpropanamido)methyl)benzoate (712 mg, 2.15 mmol) in THF:MeOH:H2O (2:1:1; 8 mL) and NaOH (344 mg, 8.60 mmol) to afford 510 mg of the title product. 1H NMR (400 MHz, DMSO-d6): δ 8.08-8.05 (t, J=8.0 Hz, 1H), 7.36-7.33 (m, 2H), 4.90 (t, 1H), 4.29-4.28 (d, J=6.0 Hz, 2H), 3.38 (m, 2H), 1.06 (s, 6H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a8ca33200b7543b89da6db1832c5179c
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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