7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester → 3-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acid

HRID 985493ノート

反応式

HRID 985493 の反応式
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][S:26][C:25]=4[CH:34]=3)[N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>C1COCC1>[N:16]1[C:17]2[NH:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[CH:14][C:15]=1[CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:28]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][S:26][C:25]=2[CH:34]=1

参加物

3

反応物 1

HCID 695482037-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 225070693-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acid収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

7-{2-[3-(2-Carboxy-ethyl)-benzo[b]thiophen-6-yloxy]-ethyl}-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (168 mg, 0.35 mmol) was dissolved in THF (10 ml). Hydrogen chloride gas was bubbled through the solution until the starting material disappears by TLC. Then the solvent was evaporated under vacuum and the crude was chromatographied over silica gel using 5% methanol/ methylene chloride as solvent to yield 32 mg (24%) of 3-{6-[2-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)-ethoxy]-benzo[b]thiophen-3-yl}-propionic acid. NMR 1H Cl3CD δ: 7.55 (d, 1H, J=8.7 Hz), 7.25 (m, 2H), 6.93 (s, 1H), 6.88 (dd, 1H, J=2.1, 8.7 Hz), 6.43 (d, 1H, J=7.2 Hz), 4.24 (t, 2H, J=6.1 Hz), 3.45 (m, 2H), 3.10 (m, 4H), 2.71 (m, 4H), 1.88 (m, 2H). Mass Spectrum (LCMS, ESI) calculate for C21H23N2O3S 383.14 (M+H) found: 383.3.

後処理

  1. customHydrogen chloride gas was bubbled through the solution until the starting material
  2. customThen the solvent was evaporated under vacuum

出典と根拠

ORDレコード
ord-d87ea9a67fde44fcb6172273a4ab4010
出典データセット
uspto-grants-2005_03
特許番号
US06872730B2

反応ノート

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