Water → Tert-butyl (2S)-4-{4-[({4-[(4-chlorophenyl)sulfonyl]cyclohexyl}carbonyl)(methyl)amino]-2-methylbenzyl}-2-methylpiperazine-1-carboxylate

HRID 2170289Notes

Reaction equation

HRID 2170289 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)=[C:4]([CH3:23])[CH:3]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([C@H:34]2[CH2:39][CH2:38][C@H:37]([C:40]([OH:42])=O)[CH2:36][CH2:35]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1.O.[CH3:44]N(C)C=O>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH:34]2[CH2:39][CH2:38][CH:37]([C:40]([N:1]([CH3:44])[C:2]3[CH:7]=[CH:6][C:5]([CH2:8][N:9]4[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C@@H:11]([CH3:22])[CH2:10]4)=[C:4]([CH3:23])[CH:3]=3)=[O:42])[CH2:36][CH2:35]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 59262126tert-butyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methylpiperazine-1-carboxylateHCID 178525783HCID 178525783, compound2×

Product 1

HCID 86700730Tert-butyl (2S)-4-{4-[({4-[(4-chlorophenyl)sulfonyl]cyclohexyl}carbonyl)(methyl)amino]-2-methylbenzyl}-2-methylpiperazine-1-carboxylateYield 45%

Procedure

To a solution of tert-butyl (2S)-4-[(4-amino-2-methylphenyl)methyl]-2-methylpiperazine-1-carboxylate (90.6 mg, 0.30 mmol), which is a known compound, and trans-4-[(4-chlorophenyl)sulfonyl]cyclohexanecarboxylic acid (100 mg, 0.30 mmol) synthesized in (10C) in N,N-dimethylformamide (8 mL), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholium chloride hydrate (106 mg, 0.36 mmol) was added at room temperature, and then, the resulting mixture was stirred at the same temperature for 20 hours. Then, to the reaction solution, water was added, and extraction was performed once with ethyl acetate. The obtained organic layer was washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20 to 50:50 (v/v)), whereby the title compound was obtained as an oil (80.2 mg, yield: 45%).

Workup

  1. additionwas added at room temperature
  2. extractionextraction
  3. washThe obtained organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20 to 50:50 (v/v)), whereby the title compound

Sources & evidence

ORD record
ord-542d8d3913fc46fe86eac157e4624e85
Source dataset
uspto-grants-2015_06
Patent number
US09051255B2

Reaction notes

Loading…