Sodium hydride → HCID 21474704, compound

HRID 1901741Notes

Reaction equation

HRID 1901741 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[NH:11][CH2:10]1.Br[CH:19]([CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH:19]([CH2:25][CH2:26][CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79071Ethyl 2-bromovalerateHCID 21474759HCID 21474759, compound

Product 1

HCID 21474704HCID 21474704, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 1.35 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 6.00 g of 5-(3-chlorophenoxymethyl)oxazolidin-2-one, 100 ml of anhydrous dimethylformamide and 6.48 g of ethyl 2-bromovalerate were used. The resulting crude product was applied to a silica gel chromatography column, and eluted, using a 1:3 by volume mixture of ethyl acetate and hexane as the eluent, to give a polar diastereomer and a less polar diastereomer separately. From the polar diastereomer, 4.5 g of the title compound having an Rf value of 0.58 (on silica gel thin layer chromatography, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent) were obtained, and from the less polar diastereomer, 4.47 g of the title compound, melting at 43° C. to 49° C., were obtained.

Workup

  1. customA procedure similar to that described in Preparation 4
  2. washeluted
  3. additionby volume mixture of ethyl acetate and hexane as the eluent
  4. customto give a polar diastereomer

Sources & evidence

ORD record
ord-3f1a2893e02447fdb29e12d6e0cb4e4f
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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