Methyl iodide → HCID 13896291, compound

HRID 489438

Reaction equation

HRID 489438 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16]C([O-])(C)C.[K+].CI>C1COCC1>[C:1]([N:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:16])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 15933116Ethyl 3-{[(tert-butoxy)carbonyl]amino}propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13896291HCID 13896291, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-aminopropionate hydrochloride (19 g) in THF (600 mL) was added triethylamine (44 mL), dimethylaminopyridine (1.5 g) and di-tert-butyldicarbonate (30 g) at 0° C. and the mixture was stirred at 40° C. for four hours. The mixture was extracted with ethyl acetate and the solvent was evaporated under reduced pressure to give ethyl N-Boc-3-aminopropionate (16.7 g) as a colorless oil. To a solution of ethyl N-Boc-3-aminopropionate (5.0 g) in THF (50 mL) was added t-BuOK (2.8 g) and methyl iodide (4.9 g) at 0° C. and the mixture was stirred at room temperature for an hour. The mixture was extracted with ethyl acetate and the solvent was evaporated under reduced pressure to give ethyl 3-(N-Boc-N-methylamino)propionate (4.3 g) as a colorless oil. Subsequently, the title compound was prepared from ethyl 3-(N-Boc-N-methylamino)propionate, 2,1,3-benzoxadiazole-4-aldehyde and 3-aminopyrazole in the same manner as in Example 1001.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9b511dd3cc9c487b887e8544ea58c8b6
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Linked notes

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