Lithium hydroxide, monohydrate → HCID 71604239, compound

HRID 2363875Notes

Reaction equation

HRID 2363875 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]([N: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>[F:30][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:31])=[O:2])[C:14]([CH3:15])=[C:13]2[CH:16]1[CH2:21][CH2:20][N:19]([S:22]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)(=[O:23])=[O:24])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686917HCID 86686917, compound

Product 1

HCID 71604239HCID 71604239, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (86.5 mg, 0.193 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (92.4 mg, 2.2 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred overnight under a nitrogen atmosphere. The solvent was evaporated. Water (20 mL) was added and the mixture was acidified with 1.0 N aqueous HCl (4 mL). The resulting white precipitate was collected by filtration, washed with water and hexanes, and dried under high vacuum to give {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (55.7 mg, 66%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s., 1H), 8.07 (br. s, 1H), 7.90 (dd, J=9.0, 6.5 Hz, 1H), 7.69 (s, 1H), 7.35 (td, J=8.5, 2.0 Hz, 1H), 3.78 (br. s., 4H), 3.22-3.43 (m, 5H), 3.09 (br. s., 2H), 2.42 (br. s., 3H), 1.81-1.97 (m, 4H), 1.67 (bd, 2H). MS cald. for C22H28FN2O4S [(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

Sources & evidence

ORD record
ord-43580e8337ca499d97e016d81deec737
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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