Diisopropylethylamine → N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valine ethyl ester

HRID 1851830Notes

Reaction equation

HRID 1851830 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:11])[C@H:6]([CH:8]([CH3:10])[CH3:9])[NH2:7])[CH3:3].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]1[O:21][C:20](=[O:22])[C:19]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:18]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH2:2]([O:4][C:5](=[O:11])[C@H:6]([CH:8]([CH3:10])[CH3:9])[NH:7][C:20]([C:19]1([NH:18][C:17]([C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:22])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 87181Ethyl L-valinate hydrochlorideHCID 247399602-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 57672852N-[[1-[(2-Furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 ml of dimethylformamide was added to a flask charged with 5 g (27 mmol) of L-valine ethyl ester hydrochloride and 5 g (22.8 mmol) of 2-(2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one. Then, 3.53 g (27.4 mmol) of diisopropylethylamine was added thereto, and the mixture was stirred for 3 days. After the solvent was distilled off under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with a 10% aqueous potassium hydrogensulfate solution and saturated brine, followed by drying with sodium sulfate. After the solvent was distilled off under reduced pressure, it was purified by silica gel chromatography to obtain 8.3 g (quantitative) of the title compound.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was successively washed with a 10% aqueous potassium hydrogensulfate solution and saturated brine
  4. dry with materialby drying with sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure, it
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-b6e7ae33a48942cbadd771f0f7842801
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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