Diisopropylamine → HCID 22959069, compound

HRID 1715247Notes

Reaction equation

HRID 1715247 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[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>[C:11]([O:10][C:8]([NH:15][CH2:16][CH2:17][C:18]([N:4]([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])=[O:19])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 8471TriethylamineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 1670692-Chloro-1-methylpyridinium iodide

Product 1

HCID 22959069HCID 22959069, compoundYield 140.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

To a mixture of diisopropylamine (280 μl; 1.99 mmol; 1 eq) and boc-beta-alanine (414.7 mg; 2.19 mmol; 1.10 eq) in DCM (30 ml), are added triethylamine (829 μl; 5.98 mmol; 3 eq) and 2-chloro-1-methylpyridinium iodide (1 527 mg; 5.98 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 layers are dried over Na2SO4, filtered and concentrated to give 760 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 (511.2 mg; 94%).

Workup

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

Sources & evidence

ORD record
ord-77b0c8a1e51b481fbd9f1f76d6dcdfdf
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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