반응 #313369

ord-f22f759269f94f20a695e382e20cecf6

반응 방정식

O=S(=O)(Cl)c1ccccc1
Benzenesulfonyl chloride
COC(=O)CCCCCN.Cl
methyl 6-aminohexanoate hydrochloride
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
COC(=O)CCCCCNS(=O)(=O)c1ccccc1
title compound
COC(=O)CCCCCNS(=O)(=O)c1ccccc1
6-Benzenesulfonylaminohexanoic acid methyl ester

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출the product was extracted with ethyl acetate (30 ml)
  2. 2
    건조The extract was dried (Na2SO4) and solvents
  3. 3
    기타were removed under reduced pressure
  4. 4
    기타The product was chromatographed on silica gel with ethyl acetate-hexane (1:2) as eluent

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 (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).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07557140B2uspto-grants-2009_07