Hydrochloric Acid → [4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid

HRID 1929581Notes

Reaction equation

HRID 1929581 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[O:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1.[OH-].[Li+].Cl>O1CCCC1>[CH2:27]([S:24]([N:21]1[CH2:22][CH2:23][N:18]([C:16]([C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=3)[CH:6]=[C:5]([CH2:4][C:3]([OH:30])=[O:2])[C:14]=2[CH3:15])=[O:17])[CH2:19][CH2:20]1)(=[O:25])=[O:26])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59326736[4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 59326748[4-(4-Ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acidYield 47.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (36 mg, 0.08 mmol) in tetrahydrofuran (4 mL), was added 5N lithium hydroxide (6 mL). After being stirred at room temperature overnight, the resulting mixture was acidified to pH 3 with 5N hydrochloric acid, and extracted with ethyl acetate (10 mL×2). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative HPLC (gradient elution with 30-50% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes) to give [4-(4-ethanesulfonyl-piperazine-1-carbonyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (16 mg, 46%) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.95 (dd, J=8.97, 5.68 Hz, 1H), 7.87 (s, 1H), 7.26-7.38 (m, 2H), 3.95-4.16 (m, 2H), 3.90 (s, 2H), 3.48-3.55 (m, 2H), 3.20 (br. s, 6H), 2.41 (s, 3H), 1.34 (t, J,=,7.45 Hz, 3H); MS cald. for C20H23FN2O5S 422, obsd. (ESI+) [(M+H)+] 423.

Workup

  1. extractionextracted with ethyl acetate (10 mL×2)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative HPLC (gradient elution with 30-50% 0.1% trifluoroacetic acid in water in acetonitrile, 8 minutes)

Sources & evidence

ORD record
ord-4663858a7b834e6bb655a0348d4754d8
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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