Water → HCID 58147668, compound

HRID 1944116Notes

Reaction equation

HRID 1944116 reaction equation
[C:1]([N:5]([CH3:29])[C:6]([C:8]1[N:12]2[CH2:13][CH2:14][C:15]3[C:20]([C:11]2=[C:10]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH:9]=1)=[CH:19][C:18]([OH:21])=[C:17]([O:22][CH3:23])[CH:16]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([O:32][C:33](=[O:36])[CH2:34]Br)[CH3:31].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH2:30]([O:32][C:33](=[O:36])[CH2:34][O:21][C:18]1[CH:19]=[C:20]2[C:15]([CH2:14][CH2:13][N:12]3[C:8]([C:6](=[O:7])[N:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH3:29])=[CH:9][C:10]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)=[C:11]32)=[CH:16][C:17]=1[O:22][CH3:23])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 58147551HCID 58147551, compound

Product 1

HCID 58147668HCID 58147668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product of example 52 (250 mg), bromo-acetic acid ethyl ester (81 μl) and Cs2CO3 (595 mg) in DMF (10 ml) was stirred at 90° C. for 1 h. The reaction mixture was allowed to cool to room temperature, subsequently poured into water and extracted with dichloromethane. The organic layer was washed with an aqueous HCl solution (0.5 M), brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel in heptane/ethyl acetate [1/1 (v/v)] as eluent.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with an aqueous HCl solution (0.5 M), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel in heptane/ethyl acetate [1/1 (v/v)] as eluent

Sources & evidence

ORD record
ord-beca9cc2987244738a887a739295f591
Source dataset
uspto-grants-2013_03
Patent number
US08394789B2

Reaction notes

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