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

HRID 386711

Reaktionsgleichung

Reaktionsgleichung von HRID 386711
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 66797535HCID 66797535, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e8c18e980a8440dd91d4abaf57117a64
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372845B2

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