Triethylamine → HCID 131728332, compound

HRID 1715248Notes

Reaction equation

HRID 1715248 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]([NH:14][CH2:15][CH2:16][C:17](O)=[O:18])([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>[C:10]([O:9][C:7]([NH:14][CH2:15][CH2:16][C:17]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:18])=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 131728332HCID 131728332, compoundYield 127%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a mixture of 2-amino-2-methyl-1-propanol (177.4 mg; 1.99 mmol; 1 eq) and boc-beta-alanine (338.9 mg; 1.79 mmol; 0.9 eq) in DCM (30 ml), are added triethylamine (0.83 ml; 5.97 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1525 mg; 5.97 mmol; 3 eq). The mixture is stirred for 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 592 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 compound is isolated as a slightly yellow solid (331.1 mg; 64%).

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-c39fbd2c59944ca68c55d766df362032
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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