Benzyl Bromide → HCID 18794787, compound

HRID 362278Notes

Reaction equation

HRID 362278 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[N:12]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[CH3:13].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O.O>[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[N:12]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[CH3:13]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18794827HCID 18794827, compound

Product 1

HCID 18794787HCID 18794787, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.14 g) was added portionwise to a stirred solution of methyl 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-hydroxypropanoate (1.20 g) in dry N,N-dimethyl formamide (20 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature for 15 minutes prior to the addition of benzyl bromide (0.6 mL). Stirring was continued at room temperature for 3 hrs, then at 80° C. for 17 hrs before the mixture was cooled, diluted with water (500 mL) and extract with ethyl acetate (3×200 mL). The combined ethyl acetate layers were washed with water (4×500 mL) and brine (500 mL), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 1% methanol in dichloromethane to afford the title compound, a gum, which was used in the next stage without further purification.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 3 hrs
  3. temperatureat 80° C. for 17 hrs before the mixture was cooled
  4. extractionextract with ethyl acetate (3×200 mL)
  5. washThe combined ethyl acetate layers were washed with water (4×500 mL) and brine (500 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-5cf10221f53f4179bb2dfabc324125fa
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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