Triethylamine → HCID 86621989, compound

HRID 1715250Notes

Reaction equation

HRID 1715250 reaction equation
[CH3:1][C:2]1([CH3:7])[NH:6][CH2:5][CH2:4][S:3]1.[C:8]([NH:15][CH2:16][CH2:17][C:18](O)=[O:19])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:1][C:2]1([CH3:7])[N:6]([C:18](=[O:19])[CH2:17][CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:5][CH2:4][S:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 880152,2-DimethylthiazolidineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 86621989HCID 86621989, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a mixture of 2,2-dimethylthiazolidine (234.4 mg; 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 2 days 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 497 mg 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 white-off solid (45.5 mg; 8%).

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-ffb61fd1172f4d0e817697f5fb07b602
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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