Tert-Butylamine → HCID 25239132, compound

HRID 1715249Notes

Reaction equation

HRID 1715249 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[C:6]([NH:13][CH2:14][CH2:15][C:16](O)=[O:17])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[C:9]([O:8][C:6]([NH:13][CH2:14][CH2:15][C:16]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 25239132HCID 25239132, compoundYield 130.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a mixture of tert-butylamine (210 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 (1 533 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 639 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 (467.7 mg; 96%).

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-e8da24cdc3294950929a8fbd95906841
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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