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

HRID 351093Notes

Reaction equation

HRID 351093 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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 (1.28 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).

Workup

  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

Sources & evidence

ORD record
ord-38fe20f6332d4c4e924b82cd75dd348c
Source dataset
uspto-grants-2007_02
Patent number
US07183298B2

Reaction notes

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