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

HRID 1929581노트

반응식

HRID 1929581 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4663858a7b834e6bb655a0348d4754d8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188090B2

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