Sodium hydride → HCID 59409899, compound

HRID 2066823Notes

Reaction equation

HRID 2066823 reaction equation
[H-].[Na+].[Cl:3][CH2:4][C:5]1([CH3:11])[O:9][C:8](=[O:10])[NH:7][CH2:6]1.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1>CN(C)C=O>[Cl:3][CH2:4][C:5]1([CH3:11])[O:9][C:8](=[O:10])[N:7]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 14698772HCID 14698772, compound2×

Product 1

HCID 59409899HCID 59409899, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture was sodium hydride (401 mg, 60% dispersion) in 50 ml of dimethylformamide was added 5-(chloromethyl)-5-methyl-1,3-oxazolidin-2-one (1.00 g, INTERMEDIATE 16) followed by 4-methoxybenzylchloride (1.05 g). The mixture was stirred at 90° C. for 4 h. Excess sodium hydride was quenched by addition of 3 ml of methanol. The sample was then transferred to a Biotage 65i column and purified via column chromatography on a Biotage Horizon eluting with 0% ethyl acetate in hexanes (1 column volume), followed by a gradient to 50% ethyl acetate in hexanes (over 6 column volumes), and held at 50% ethyl acetate (2 column volumes) to provide the title compound (1.41 g, 78%). Mass spectrum (ESI) 271.9 (M+2).

Workup

  1. customExcess sodium hydride was quenched by addition of 3 ml of methanol
  2. custompurified via column chromatography on a Biotage Horizon
  3. washeluting with 0% ethyl acetate in hexanes (1 column volume)

Sources & evidence

ORD record
ord-40bb9871aeca4f3188685fb308f21d60
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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