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

HRID 324333Notes

Reaction equation

HRID 324333 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-19202f9f675c4e30b82e060d5cd28859
Source dataset
uspto-grants-2001_04
Patent number
US06218390B1

Reaction notes

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