Lithium hydroxide, monohydrate → HCID 71711649, compound

HRID 1468449Notes

Reaction equation

HRID 1468449 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:30])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][N:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:29])[CH:14]=2)[CH:9]=1>C1COCC1.O>[F:29][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:30])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86695028HCID 86695028, compound

Product 1

HCID 71711649HCID 71711649, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (0.0045 g, 0.107 mmol) was added to a mixture of [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid methyl ester (0.014 g, 0.036 mmol) in a 1:1 mixture of THF—H2O mixture (2 mL). The reaction mixture was stirred for 5 hours at room temperature. The reaction mixture was concentrated to remove the THF, and the aqueous residue was combined with a 1.0 N aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate. The collected organic layers were dried over anhydrous MgSO4, filtered, and concentrated to provide [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid (0.009 g) as a white solid. The final product contained a significant amount of water as an impurity. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.35 (br. s, 1 H), 9.26 (dd, J=2.42, 0.60 Hz, 1 H), 8.49 (dd, J=8.00, 2.26 Hz, 1 H), 8.03 (dd, J=8.80, 6.80 Hz, 1 H), 7.95 (s, 1 H), 7.73 (d, J=8.15 Hz, 1 H), 7.40 (td, J=8.80, 2.40 Hz, 1 H), 6.75 (dd, J=11.00, 2.40 Hz, 1 H), 3.87 (s, 2 H), 3.45 (s, 3 H), 2.07 (s, 3 H). MS calcd. for C19H17FNO4S [(M+H)+] 374, obsd. 374.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the THF
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe collected organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9b5c72994a946c89c5a3dcc58564e9e
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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