Triethylamine → HCID 57925600, compound

HRID 1715252Notes

Reaction equation

HRID 1715252 reaction equation
[CH2:1]([NH2:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:7]([NH:14][CH2:15][C:16](O)=[O:17])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH3:3][C:2]([CH3:5])([CH3:4])[CH2:1][NH:6][C:16](=[O:17])[CH2:15][NH:14][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 79882NeopentylamineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 57925600HCID 57925600, compoundYield 193.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a mixture of neopentylamine (174.3 mg; 2 mmol; 1 eq) and boc-glycine (385.4 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 946 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 slightly yellow solid (96.7 mg; 20%).

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-865743b3b3c24e5380b25b714469f11d
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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