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

HRID 2180445

반응식

HRID 2180445 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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 δH (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).

후처리

  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

출처 및 근거

ORD 기록
ord-dce5aa16e0924a708609dc37d6e30950
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06888027B2

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