Hydrochloric Acid → HCID 71711573, compound

HRID 1468444Notes

Reaction equation

HRID 1468444 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:26])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:26][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:27])=[O:2])[C:14]([CH3:15])=[C:13]2[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86695025HCID 86695025, compound

Product 1

HCID 71711573HCID 71711573, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [6-fluoro-4-(4-methansulfonyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (77.7 mg, 0.2 mmol) in THF (10 mL) was added a solution of lithium hydroxide monohydrate (83.92 mg, 2.0 mmol) in water (2 mL) at room temperature. The resulting clear solution was stirred for 15 hours. The reaction mixture was concentrated to remove THF. The residue was diluted with water (˜30 mL) to obtain a clear solution. The basic aqueous layer was acidified with 1.0 N hydrochloric acid. The precipitated solids were collected by filtration and washed with water and hexanes. After drying in air, [6-fluoro-4-(4-methansulfonyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid (65 mg, 87%) was isolated as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 8.11 (d, J=8.2 Hz, 2 H), 8.02 (dd, J=9.0, 6.0 Hz, 1 H), 7.92 (s, 1 H), 7.54 (d, J=8.2 Hz, 2 H), 7.39 (td, J=9.0, 2.3 Hz, 1 H), 6.71 (dd, J=11.3, 2.3 Hz, 1 H), 3.86 (s, 2 H), 3.35 (s, 3 H), 2.08 (s, 3 H). HRMS calcd. for C20H18FO4S [(M+H)+] 373.0905, obsd. 373.0904.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionThe residue was diluted with water (˜30 mL)
  4. customto obtain a clear solution
  5. filtrationThe precipitated solids were collected by filtration
  6. washwashed with water and hexanes
  7. customAfter drying in air

Sources & evidence

ORD record
ord-986438748f074c3aa868531fe694a2f8
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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