Diisopropylethylamine → HCID 58355735, compound

HRID 1509615Notes

Reaction equation

HRID 1509615 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[N:16]=[N:17][N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:3]1.C(N(C(C)C)CC)(C)C.Br[CH2:49][CH2:50][CH2:51][CH2:52][C:53](Cl)=[O:54]>C1COCC1.O>[CH3:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]1[N:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:17]=[N:16][C:15]=1[C:13]([N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C@@H:6]1[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:3][C@H:2]([N:1]2[CH2:49][CH2:50][CH2:51][CH2:52][C:53]2=[O:54])[CH2:7]1)=[O:14]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 58355545HCID 58355545, compound

Product 1

HCID 58355735HCID 58355735, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (3R,5S)-3-amino-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate (150 mg) was dissolved in THF (3 ml), diisopropylethylamine (74 μl) and 5-bromovaleryl chloride (42 μl) were added at 0° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in THF (10 ml), potassium tert-butoxide (96 mg) was added at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (1:3-1:0) was concentrated under reduced pressure to give the object product (150 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in THF (10 ml)
  6. additionpotassium tert-butoxide (96 mg) was added at 0° C.
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionthe residue was diluted with water
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe extract was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. washa fraction eluted with ethyl acetate-hexane (1:3-1:0)
  15. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a73709c8ce345f3864fabee74fe1623
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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