Ethyl bromoacetate → HCID 86753642, compound

HRID 850386Notes

Reaction equation

HRID 850386 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25]>CN(C=O)C>[CH2:24]([O:26][C:27](=[O:30])[CH2:28][O:17][C:11]1[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=1[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 11311441N-t-Butoxycarbonyl-2-Hydroxy-5-Chlorobenzylamine

Product 1

HCID 86753642HCID 86753642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-t-butoxycarbonyl-2-hydroxy-5-chlorobenzylamine (730 mg, 2.83 mmol), Cs2CO3 (923 mg, 2.83 mmol) and ethylbromoacetate (0.314 ml, 2.83 mmol) in DMF (5 ml) was stirred for 2 h. The crude reaction mixture was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried (Na2SO4) and evaporated in vacuo to an oil which was used for the next step.

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo to an oil which

Sources & evidence

ORD record
ord-b95815e639a24d64816a643ab534f762
Source dataset
uspto-grants-2000_01
Patent number
US06017934

Reaction notes

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