Tert-butoxycarbonylalanine → N-(tert-Butoxycarbonyl)-L-alanine 4-(2-pyridyl)piperidin-1-yl amide

HRID 1860423Notes

Reaction equation

HRID 1860423 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl.C[N:28](C)CCCN=C=NCC>ClCCl>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[CH2:25][CH2:24][N:23]([NH:28][C:11](=[O:13])[C@H:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103747502-(Piperidin-4-yl)pyridine

Product 1

HCID 18712694N-(tert-Butoxycarbonyl)-L-alanine 4-(2-pyridyl)piperidin-1-yl amideYield 107.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-alanine (1.485 g, 7.847 mmol) and 4-(2-pyridyl)piperidine (0.910 g, 5.60 mmol) in dichloromethane (20 mL) at 0° C., was added N,N-dimethylaminopyridine (DMAP, 2.05 g, 16.8 mmol) and 1-(3-dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (DMAPECD, 2.147 g, 11.2 mmol). The resulting mixture was stirred overnight while warmed up to room temperature. The reaction mixture was quenched with aqueous NH4Cl (30 mL) and extracted with CH2Cl2 (30 mL×2). The combined extracts were dried (K2CO3), concentrated, and purified by flash chromatography on silica gel (100% EtOAc) to obtain 2.09 g (80%) of N-(tert-Butoxycarbonyl)-L-alanine 4-(2-pyridyl)piperidin-1-yl amide.

Workup

  1. customThe reaction mixture was quenched with aqueous NH4Cl (30 mL)
  2. extractionextracted with CH2Cl2 (30 mL×2)
  3. dry with materialThe combined extracts were dried (K2CO3)
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-3f69b16320744df4a7169b5d921874a5
Source dataset
uspto-grants-2003_03
Patent number
US06531471B2

Reaction notes

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