Triethylamine → HCID 28801823, compound

HRID 1715253Notes

Reaction equation

HRID 1715253 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])C.[I-].ClC1C=[CH:27][CH:26]=[CH:25][N+]=1C.C1CCCCC1.CCOC(C)=O>C(Cl)Cl>[N:16]1([C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:17][CH2:18][CH2:27][CH2:26][CH2:25][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 28801823HCID 28801823, compoundYield 170.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of heptamethyleneimine (254 μl; 2 mmol; 1 eq) and boc-beta-alanine (416.3 mg; 2.20 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (832 μl; 6 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1533 mg; 6 mmol; 3 eq). The mixture is stirred overnight at RT. The reaction is followed by TLC (cyclohexane/EtOAc 1:1). The reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated to give 1.066 g of an orange oil, which is purified by flash chromatography (cyclohexane/EtOAc gradient, from 9/1 to 1/1 over 30 min). The title product is isolated as a slightly yellow solid (477 mg; 84%).

Workup

  1. washThe reaction mixture is then washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f5e8367d74174a93a22df1e1fa81e65f
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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