Triethylamine → (S)-tert-Butyl 2-((S)-2-(6-bromopyridin-3-yl)-1-cyanoethylcarbamoyl)piperidine-1-carboxylate

HRID 600305Notes

Reaction equation

HRID 600305 reaction equation
C(N(CC)CC)C.ClS(NC(=O)OC)(=O)=O.[NH2:17][C:18](=O)[C@@H:19]([NH:28][C:29]([C@@H:31]1[CH2:36][CH2:35][CH2:34][CH2:33][N:32]1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:30])[CH2:20][C:21]1[CH:22]=[N:23][C:24]([Br:27])=[CH:25][CH:26]=1>C(Cl)Cl>[Br:27][C:24]1[N:23]=[CH:22][C:21]([CH2:20][C@H:19]([NH:28][C:29]([C@@H:31]2[CH2:36][CH2:35][CH2:34][CH2:33][N:32]2[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:30])[C:18]#[N:17])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10702364Methyl chlorosulfonylcarbamateHCID 57999667(S)-tert-Butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57999686(S)-tert-Butyl 2-((S)-2-(6-bromopyridin-3-yl)-1-cyanoethylcarbamoyl)piperidine-1-carboxylateYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Triethylamine (3.46 mL) in DCM (5 mL) was stirred under nitrogen and to the solution was added a solution of methyl chlorosulfonylcarbamate (1.658 g) in DCM (5 mL). The mixture was stirred at room temperature for 15 min then a solution of (S)-tert-butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (1.74 g) in DCM (5 mL) was added. Stirring was continued overnight. The reaction mixture was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane to give the title compound (1.2 g) as a white solid.

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. washThe reaction mixture was washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customCrude product was purified by flash silica chromatography
  8. washeluting with 40% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-bc77143b74e1415f94e4d464787c0575
Source dataset
uspto-grants-2011_03
Patent number
US07902181B2

Reaction notes

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