Benzenesulfonyl chloride → Hexanoic acid, 6-[(phenylsulfonyl)amino]-, methyl ester

HRID 351093

반응식

HRID 351093 반응식
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[CH3:21][O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][NH:12][S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8]

참가 물질

6

반응물 3

HCID 7369Benzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 11499324Methyl 6-aminohexanoate hydrochloride

생성물 1

HCID 15295437Hexanoic acid, 6-[(phenylsulfonyl)amino]-, methyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Benzenesulfonyl chloride (92a) (0.88 g, 5.0 mmol) was added to the mixture of methyl 6-aminohexanoate hydrochloride (91) (1.82 g, 10 mmol) in acetonitrile (10 ml) and sodium carbonate (2.6 g, 24.6 mmol) in water (10 ml). The mixture was stirred for 6 hours at ambient temperature, and the product was extracted with ethyl acetate (30 ml). The extract was dried (Na2SO4) and solvents were removed under reduced pressure. The product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent. The title compound was obtained as oil (1.28 g, 90%). 1H NMR δH (90 MHz, DMSO-d6) δ: 0.90–1.63 (6H, m, CH2); 2.21 (2H, t, J=7.0 Hz, CH2); 2.71 (2H, q, J=6.0 Hz, CH2N); 3.58 (3H, s, CH3); 7.40–7.72 (3H, m, C6H3); 7.72–7.89 (2H, m, C6H2).

후처리

  1. extractionthe product was extracted with ethyl acetate (30 ml)
  2. dry with materialThe extract was dried (Na2SO4) and solvents
  3. customwere removed under reduced pressure
  4. customThe product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent

출처 및 근거

ORD 기록
ord-38fe20f6332d4c4e924b82cd75dd348c
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183298B2

연결된 노트

불러오는 중…