Ethyl bromoacetate → HCID 19605580, compound

HRID 1603949Notes

Reaction equation

HRID 1603949 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:18])([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[C:8]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:7]=[CH:6][C:5]=1[O:18][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 19605595HCID 19605595, compound

Product 1

HCID 19605580HCID 19605580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-1 (5 g, 19.7 mmol) in DMF (125 mL) was treated with cesium carbonate (3.17 g, 9.73 mmol), stirred for 10 minutes and treated with ethyl bromoacetate (2.2 mL, 19.8 mmol) at room temperature. After 1.5 hours the solution was concentrated under high vacuum and the residue was absorbed to silica gel and chromatographed in a gradient of 20 to 30% EtOAc/hexanes to give 5-2 as a bright yellow solid.

Workup

  1. concentrationAfter 1.5 hours the solution was concentrated under high vacuum
  2. customthe residue was absorbed to silica gel
  3. customchromatographed in a gradient of 20 to 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-2235ff171572421d8a44e5e5c6947da3
Source dataset
uspto-grants-1999_11
Patent number
US05990107

Reaction notes

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