Triethylamine → HCID 88218721, compound

HRID 565409Notes

Reaction equation

HRID 565409 reaction equation
[C:1]([N:8]([CH3:15])[CH:9](C)[CH2:10][CH2:11][CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]1([CH3:26])[C:17]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[C:16]1([CH3:26])[C:17]([S:22]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH3:15])(=[O:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 22390115HCID 22390115, compound

Product 1

HCID 88218721HCID 88218721, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round bottom flask, charged with 4.75 g (23.4 mmol) of N-BOC-N-methyl-4-aminopentanol (32) in 150 mL of methylene chloride, was added 5.25 g (27.5 mmol) of toluenesulfonyl chloride and 7.0 mL (49.6 mmol) of triethylamine. The mixture was stirred at room temperature for 24 h and then washed with 3×75 mL aliquots of 1 N aqueous HCl. The organic phase was dried over anhydrous magnesium sulfate, vacuum filtered, and concentrated via rotary evaporation. The residue was chromatographed on silica gel, eluting first with 20% ethyl acetate/hexane and then with 30% ethyl acetate/hexane. The fractions containing product (33) were combined and concentrated via rotary evaporation to afford 6.95 g of the product as a very pale yellow oil (83%): 1H-NMR (CDCl3) d 7.78 (2H, d), 7.31 (2H, d), 4.03 (2H, t), 3.15 (2H, t), 2.86 (3H, s), 2.42 (3H, s), 1.73-1.47 (4H, m), and 1.41 (9H, s) ppm.

Workup

  1. washwashed with 3×75 mL aliquots of 1 N aqueous HCl
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate, vacuum
  3. filtrationfiltered
  4. concentrationconcentrated via rotary evaporation
  5. customThe residue was chromatographed on silica gel
  6. washeluting first with 20% ethyl acetate/hexane
  7. additionThe fractions containing product (33)
  8. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-44a89c4674744b559bccc693f2ff9958
Source dataset
uspto-grants-2001_01
Patent number
US06172045B2

Reaction notes

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