Benzenesulfonyl chloride → HCID 53845907, compound

HRID 369108Notes

Reaction equation

HRID 369108 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([CH2:12][NH:13][CH3:14])[CH2:9][CH:10]=[CH2:11])[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([CH2:9][CH:10]=[CH2:11])[CH2:12][N:13]([CH3:14])[S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21971891HCID 21971891, compound

Product 1

HCID 53845907HCID 53845907, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g (9.53 mmol) of (S)-4-(3-chorophenyl)-5-methylamino-1-pentene (prepared as described by J. Hale et al., Bioorganic and Medicinal Chemistry Letters, 1993, 3, 319-322) and 5.0 mL (28.6 mmol) of diisopropylethylamine (DIPEA) in 20 mL of methylene chloride was cooled in an ice/ethanol bath. To this was added 1.46 mL (11.4 mmol) of benzenesulfonyl chloride and after 5 min the ice bath was removed. After stirring for 16 h, the reaction mixture was diluted with methylene chloride and washed with water containing 20 mL of 2 N HCl. The aqueous layer was reextracted with methylene chloride and the organic layers were washed with brine, combined, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (FCC) eluting with 15% ethyl acetate/hexanes to afford 3.44 g of the title compound. 1H NMR (400 MHz, CDCl3): δ 2.38 (p, J=8, 1H), 2.55 (m, 1H), 2.59 (s, 3H), 2.94 (m, 2H), 3.37 (m, 1H), 4.95 (m, 2H), 5.60 (m, 1H), 7.05-7.3 (m, 4H), 7.46 (m, 2H), 7.55 (m, 1H), 7.69 (dd, J=1.5 and 6, 2H).

Workup

  1. customafter 5 min the ice bath was removed
  2. additionthe reaction mixture was diluted with methylene chloride
  3. washwashed with water containing 20 mL of 2 N HCl
  4. washthe organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (FCC)
  8. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6b2b657a508745ce96cf09f33d6d1b95
Source dataset
uspto-grants-2000_10
Patent number
US06136827

Reaction notes

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