Benzoic acid, 3-(chlorosulfonyl)-, methyl ester → HCID 66797535, 화합물

HRID 386711

반응식

HRID 386711 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 66797535HCID 66797535, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e8c18e980a8440dd91d4abaf57117a64
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372845B2

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