Water → HCID 90427833, compound

HRID 2278940Notes

Reaction equation

HRID 2278940 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]([CH3:12])[CH2:9][O:10][CH3:11])=[O:6].[H-].[Na+].CCOC(C)=O.O>C1COCC1>[CH3:11][O:10][CH2:9][C@@H:8]([N:7]1[CH2:2][CH2:3][NH:4][C:5]1=[O:6])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 90427244HCID 90427244, compound

Product 1

HCID 90427833HCID 90427833, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A −20° C. solution of (S)-1-(2-chloroethyl)-3-(1-methoxypropan-2-yl)urea (1.092 g, 5.61 mmol) in THF (25 mL) was treated portion-wise with NaH (60% in mineral oil, 505 mg, 12.62 mmol), allowed to warm to RT and stirred overnight. The mixture was treated with EtOAc, water, then 5% citric acid, the layers separated and the organic layer washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford (S)-1-(1-methoxypropan-2-yl)imidazolidin-2-one (95 mg, 11%). MS (ESI) m/z: 159.1 (M+H+).

Workup

  1. custom5% citric acid, the layers separated
  2. washthe organic layer washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-17051fdfec6d40c48cfd8d807064d1bd
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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