Sodium hydride → HCID 131722439, compound

HRID 1531936Notes

Reaction equation

HRID 1531936 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:6])[CH3:3].[H-].[Na+].[Br:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]Br)[CH:19]=1>O1CCCC1>[Br:16][CH2:17][C:18]1[CH:19]=[C:20]([CH2:24][N:7]([C:5]([O:4][C:2]([CH3:13])([CH3:1])[CH3:3])=[O:6])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69373Benzene, 1,3-bis(bromomethyl)-HCID 637609N-Boc-glycine methyl ester

Product 1

HCID 131722439HCID 131722439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of the product from step (i) (5 g) in tetrahydrofuran (10 ml) was added dropwise to a suspension of sodium hydride (1.1 g) in tetrahydrofuran (40 ml) at 0° C. The mixture was warmed to room temperature and stirred for 30 minutes then added dropwise to a solution of α,α′-dibromo-m-xylene (10.56 g) in tetrahydrofuran (40 ml). The mixture was stirred at room temperature for 2 hours, quenched with aqueous ammonium chloride and partitioned between ethyl and acetate and water. The organic phase was dried (MgSO4) and evaporated. Purified by chromatography eluting with 10% ethyl acetate in isohexane. Yield 2.8 g.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customquenched with aqueous ammonium chloride
  3. custompartitioned between ethyl and acetate and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurified by chromatography
  7. washeluting with 10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-fc16ac5647be4b3abd13ec521152faaa
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Reaction notes

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