Octylamine → HCID 21103268, compound

HRID 1354082Notes

Reaction equation

HRID 1354082 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18](CO)[C:19]([O:21][CH3:22])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29].CS(Cl)(=O)=[O:34].[CH2:37](N)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]CC>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([N:17]3[CH2:29][C:28](=[O:34])[N:27]([CH2:30][CH2:31][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:26][CH:18]3[C:19]([O:21][CH3:22])=[O:20])(=[O:16])=[O:15])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8143OctylamineHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 21103277HCID 21103277, compound

Product 1

HCID 21103268HCID 21103268, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The compound of Example 29 (2.13 g, 4.25 mmol) was suspended in 40 mL of dichloromethane, and then Et3N (0.83 mL, 5.9 mmol) and methane sulfonyl chloride (0.43 mL, 5.52 mmol) were added dropwise while maintaining the temperature at 0° C. After stirring at room temperature for 4 hours, the temperature was lowered to 0° C., and 20 mL of dichloromethane in which Et3N (1.2 mL, 8.5 mmol) and octylamine (2.1 mL, 12.7 mmol) were dissolved were added. After stirring at room temperature for 16 hours, the reactant was washed with distilled water, 2N HCl, and a saturated NaHCO3 aqueous solution, and then it was dried and concentrated under reduced pressure. The mixture was separated with ethyl acetate/hexane (4:1) in a silica gel column, and recrystallized with hexane and ethyl acetate to obtain a white title compound (1.35 g, yield 56%).

Workup

  1. customwas lowered to 0° C.
  2. additionwere added
  3. stirringAfter stirring at room temperature for 16 hours
  4. washthe reactant was washed with distilled water, 2N HCl
  5. dry with materiala saturated NaHCO3 aqueous solution, and then it was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe mixture was separated with ethyl acetate/hexane (4:1) in a silica gel column
  8. customrecrystallized with hexane and ethyl acetate

Sources & evidence

ORD record
ord-965efc08d702416e879f703dea42a4a0
Source dataset
uspto-grants-2007_05
Patent number
US07223751B2

Reaction notes

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