Triethylamine → 6-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester

HRID 2217711

反応式

HRID 2217711 の反応式
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:3]=1.Cl.[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20].C(N(CC)CC)C>C(#N)C>[CH3:22][O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][S:8]([C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 12571517Pyridine-3-sulfonyl chloride hydrochloride

生成物 1

HCID 207804896-(Pyridine-3-sulfonylamino)hexanoic acid methyl ester収率 76.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Pyridine-3-sulfonyl chloride hydrochloride (92c) (1.8 g, 5.0 mmol) was added to a solution of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in acetonitrile (30 ml). The mixture was stirred for 1 hour at ambient temperature, filtered and solvents were removed under reduced pressure. The oily product was dissolved in water (15 ml) and extracted with ethyl ether (50 ml). The extract was dried (Na2SO4) and the solvents were removed under reduced pressure. The title compound (1.09 g, 76%) was obtained as oil and was used for the next step without an additional purification. 1H NMR 5H (90 MHz, DMSO-d6) δ: 0.80-1.51 (6H, m, CH2); 1.83 (2H, t, J=6.5 Hz, CH2); 2.76 (2H, t, J=6.5 Hz, CH2N); 3.58 (3H, s, CH3); 7.54 (1H, dd, J=5.0 Hz, J=8.2 Hz, C5HN); 8.12 (1H, dt, J=2.0 Hz, J=8.2 Hz, C5HN); 8.61 (1H, dd, J=2.0 Hz, J=5.0 Hz, C5HN); 8.81 (1H, d, J=2.0 Hz, C5HN).

後処理

  1. filtrationfiltered
  2. customsolvents were removed under reduced pressure
  3. dissolutionThe oily product was dissolved in water (15 ml)
  4. extractionextracted with ethyl ether (50 ml)
  5. dry with materialThe extract was dried (Na2SO4)
  6. customthe solvents were removed under reduced pressure

出典と根拠

ORDレコード
ord-10b1d605a31e4f2e80dcb447065e860a
出典データセット
uspto-grants-2008_08
特許番号
US07407988B2

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