Triethylamine → HCID 31854483, compound

HRID 1519087Notes

Reaction equation

HRID 1519087 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.[Br:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1([NH:12][S:27]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[Br:20])(=[O:29])=[O:28])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5204032-Bromobenzenesulfonyl chlorideHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochloride

Product 1

HCID 31854483HCID 31854483, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50-mL flask, 1-amino-cyclohexanecarboxylic acid methylester hydrochloride (350 mg, 1.80 mmol) and methylenechloride (20 mL) were charged, and then triethylamine (0.836 mL, 5.99 mmol) was charged, followed by stirring for 30 minutes at room temperature. 2-bromo-benzenesulfonylchloride (383 mg, 1.49 mmol) was added thereto, followed by stirring for 12 hours at room temperature. Then, purified water (10 ml) was added thereto to bring the reaction to an end. The organic layer was separated, and washed with saturated ammonium chloride solution (20 ml). Then, the washed organic layer was separated, and added with magnesium sulfate so as to remove remaining moisture. Then, through filtering and vacuum distillation, the solvent was removed so as to obtain the residue. The mixture was purified with column chromatography (EA/n-Hex=1:5) so as to obtain 1-(2-bromo-benzenesulfonylamino)-cyclohexanecarboxylic acid methylester (285 mg, 51%).

Workup

  1. stirringby stirring for 12 hours at room temperature
  2. customThen, purified water (10 ml)
  3. additionwas added
  4. customthe reaction to an end
  5. customThe organic layer was separated
  6. washwashed with saturated ammonium chloride solution (20 ml)
  7. customThen, the washed organic layer was separated
  8. additionadded with magnesium sulfate so as
  9. customto remove
  10. filtrationThen, through filtering
  11. distillationvacuum distillation
  12. customthe solvent was removed so as
  13. customto obtain the residue
  14. customThe mixture was purified with column chromatography (EA/n-Hex=1:5) so as

Sources & evidence

ORD record
ord-95fee7669a38443e8da0c1c4f3d17a50
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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