Benzoic acid, 3-(chlorosulfonyl)-, methyl ester → HCID 66797535、化合物

HRID 386711

反応式

HRID 386711 の反応式
[C:1]([O:5][C:6]([C:8]1([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[S:15]([C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23][CH3:24])=[O:22])(=[O:17])=[O:16]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:24][O:23][C:21](=[O:22])[C:20]1[CH:25]=[CH:26][CH:27]=[C:18]([S:15](=[O:16])(=[O:17])[NH:13][CH2:12][C:8]2([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10][CH2:11]2)[CH:19]=1

参加物

5

反応物 2

HCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 667975881366068-12-3

生成物 1

HCID 66797535HCID 66797535、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 1-aminomethyl-cyclobutanecarboxylic acid tert-butyl ester (step 2) (1.47 g, 7.38 mmol) in DCM (40 ml) was treated with TEA (2.57 ml, 18.44 mmol) followed by methyl 3-(chlorosulfonyl)benzoate (1.91 g, 8.11 mmol) and DMAP (0.09 g, 0.74 mmol). The mixture was stirred at RT for 2 h and then partitioned between DCM and water. The aqueous portion was extracted with DCM and the combined organic extracts were washed with 0.1N HCl, brine, dried over MgSO4 and concentrated in vacuo. Purification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the title compound as a colourless oil; 1H NMR (400 MHz, CDCl3) δ 8.56 (1H, s), 8.27 (1H, d), 8.08 (1H, d), 7.64 (1H, t), 5.21 (1H, br t), 3.98 (3H, s), 3.20 (2H, d), 2.37 (2H, m), 1.96 (4H, m), 1.46 (9H, s).

後処理

  1. custompartitioned between DCM and water
  2. extractionThe aqueous portion was extracted with DCM
  3. washthe combined organic extracts were washed with 0.1N HCl, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the resulting oil by chromatography on silica eluting with 0-40% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-e8c18e980a8440dd91d4abaf57117a64
出典データセット
uspto-grants-2013_02
特許番号
US08372845B2

関連ノート

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