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

HRID 226187

反応式

HRID 226187 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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 (128 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).

後処理

  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

出典と根拠

ORDレコード
ord-f22f759269f94f20a695e382e20cecf6
出典データセット
uspto-grants-2009_07
特許番号
US07557140B2

関連ノート

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