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Pyridine → N~2~-(tert-Butoxycarbonyl)-L-leucinamide

HRID 927441
Notes
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Reaction equation

HRID 927441 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:32]1C=CC=CC=1.[OH-].[NH4+]>CC#N>[NH2:32][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 14923Ammonium HydroxideHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 7201299N~2~-(tert-Butoxycarbonyl)-L-leucinamideYield 86%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

A mixture of (S)-2-(tert-butoxycarbonylamino)-4-methylpentanoic acid (1.8 g), di-tert-butyl dicarbonate (CAN:24424-99-5, 12 mmol) and pyridine (3 mL) in CH3CN (50 mL) was stirred at room temperature for 20 min. Ammonium hydroxide solution (25%-28% NH3, 15 mL) was added dropwise during 30 min. The resulting reaction mixture was stirred overnight. During the removal of solvents, the product precipitated, was collected by filtration and dried to give the target compound as a white solid (1.55 g, 86%). MS (D): m/e=253.2 [M+Na]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight
  3. customDuring the removal of solvents
  4. customthe product precipitated
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-96d5367fa8bd4bf080b8db505e4aef3e
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290451B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes