Lithium hydroxide, monohydrate → HCID 71604238, compound

HRID 2363873Notes

Reaction equation

HRID 2363873 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:30])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[CH:25]1([S:22]([N:19]2[CH2:20][CH2:21][CH:16]([C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([F:30])[CH:11]=4)[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[C:14]=3[CH3:15])[CH2:17][CH2:18]2)(=[O:23])=[O:24])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686916HCID 86686916, compound

Product 1

HCID 71604238HCID 71604238, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(1-cyclopentanesulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (64.8 mg, 0.145 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (69.5 mg, 1.7 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred for three hours under a nitrogen atmosphere. The solvent was evaporated. Water (20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (3 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum. This crude product was further purified using preparative reverse-phase HPLC to give [4-(1-cyclopentane-sulfonyl-piperidin-4-yl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (19 mg, 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s., 1H), 7.97-8.17 (m, 1H), 7.90 (dd, J=9.03, 6.53 Hz, 1H), 7.69 (s, 1H), 7.35 (t, J=7.53 Hz, 1H), 3.78 (br. s., 6H), 3.11 (br. s., 2H), 2.42 (br. s., 4H), 1.96-2.08 (m, 2H), 1.80-1.93 (m, 2H), 1.53-1.78 (m, 6H). MS cald. for C23H29FNO4S [(M+H)+]: 434, obsd. 434.2.

Workup

  1. customThe solvent was evaporated
  2. additionWater (20 mL) was added
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with water and hexanes
  5. customdried under high vacuum
  6. customThis crude product was further purified

Sources & evidence

ORD record
ord-147914a1abde4d97859fbeea965553ec
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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