Benzyl bromoacetate → HCID 53681911, compound

HRID 1370657Notes

Reaction equation

HRID 1370657 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([O:33][C:34](=[O:37])CBr)[C:27]1C=CC=CC=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:25])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:34]([O:33][CH2:26][CH3:27])=[O:37])=[CH:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 62576Benzyl bromoacetateHCID 53909552HCID 53909552, compound

Product 1

HCID 53681911HCID 53681911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(N-benzylaminomethyl)benzoic acid benzyl ester (5.21 g) and bromoacetic acid benzyl ester (1.7 ml) in DMF (10 ml) was stirred for two hours at 80° C. and ice water was added thereto. The reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and a saturated aqueous solution of sodium chloride, successively. The organic layer was dried over and evaporated. The residue was purified by silica gel column chromatography to obtain the title compound (2.26 g).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, water
  3. customThe organic layer was dried over and
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7796e94838224fe19592aea66eb89356
Source dataset
uspto-grants-2003_06
Patent number
US06583177B2

Reaction notes

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