Hydrochloric Acid → HCID 71604174, compound

HRID 2363863Notes

Reaction equation

HRID 2363863 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([CH:16]2[CH2:21][CH2:20][N:19]([S:22]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:24])=[O:23])[CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+].Cl>C1COCC1.O>[F:32][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[C:14]([CH3:15])=[C:13]2[CH:16]1[CH2:21][CH2:20][N:19]([S:22]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:23])=[O:24])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86686910HCID 86686910, compound

Product 1

HCID 71604174HCID 71604174, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution [6-fluoro-3-methyl-4-(1-phenylmethanesulfonyl-piperidin-4-yl)-naphthalen-2-yl]-acetic acid methyl ester (82 mg, 0.175 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (83.8 mg, 2 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. After this time, the reaction mixture was diluted with water (˜20 mL) and then acidified with 1.0 N aqueous HCl (3.5 mL). The resulting white precipitate was collected by vacuum filtration, washed with hexanes, and then further dried under vacuum to provide [6-fluoro-3-methyl-4-(1-phenylmethane-sulfonyl-piperidin-4-yl)-naphthalen-2-yl]-acetic acid (50 mg, 63%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.43 (br. s., 1H), 7.90 (dd, J=9.03, 6.53 Hz, 1H), 7.80-8.13 (m, 1H), 7.69 (s, 1H), 7.31-7.53 (m, 6H), 4.49 (br. s., 2H), 3.66-3.85 (m, 4H), 3.46-3.57 (m, 1H), 2.87-3.20 (m, 2H), 2.41 (br. s., 3H), 2.13-2.37 (m, 2H), 1.61-1.71 (m, 2H). MS cald. for C25H27FNO4S [(M+H)+]: 456, obsd. 456.2.

Workup

  1. filtrationThe resulting white precipitate was collected by vacuum filtration
  2. washwashed with hexanes
  3. customfurther dried under vacuum

Sources & evidence

ORD record
ord-26169a50840347ecb3eb7b43125c4cf8
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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