Hydrochloric Acid → HCID 90060318, compound

HRID 1779191Notes

Reaction equation

HRID 1779191 reaction equation
Cl[S:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:4])=[O:3].[CH2:17]([NH2:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)C(C)C)(C)C.Cl>ClCCl>[CH2:17]([NH:23][S:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:4])=[O:3])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8102HexylamineHCID 81531DiisopropylethylamineHCID 90060321HCID 90060321, compound

Product 1

HCID 90060318HCID 90060318, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 8-chlorosulfonyl-octanoate (No. 6804260; 692.3 mg, 2.56 mmol) was dissolved in dichloromethane (4.0 mL), and a solution of hexylamine (310.5 mg, 3.07 mmol) in dichloromethane (3.0 mL) and N,N-diisopropylethylamine (668 μL, 3.84 mmol) were added in order. The mixture was stirred at room temperature for 22 hours. After completing the reaction, the mixture was neutralized by adding 1 M hydrochloric acid, and extracted with dichloromethane. The organic layer was washed with water and a saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off. The resulting residue was then purified with SP1 (SiO2 cartridge, 25% ethyl acetate/n-hexane, Rf=0.5) to obtain ethyl 8-hexylsulfamoyl-octanoate (No. 6804262; 818.3 mg, 95% yield).

Workup

  1. customthe reaction
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materiala saturated brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off
  7. customThe resulting residue was then purified with SP1 (SiO2 cartridge, 25% ethyl acetate/n-hexane, Rf=0.5)

Sources & evidence

ORD record
ord-5c0efd31d06c4d5c8a08fe921fd0ac45
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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