Water → HCID 131728177, compound

HRID 1695140Notes

Reaction equation

HRID 1695140 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])=[C:10]([F:21])[CH:9]=2)[CH:7]=1.[CH2:23]([O:25][C:26](=[O:29])[CH2:27]Br)[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:27][C:26]([O:25][CH2:23][CH3:24])=[O:29])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:15])=[C:10]([F:21])[CH:9]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 67276502HCID 67276502, compound

Product 1

HCID 131728177HCID 131728177, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of step c) (0.11 g) was dissolved in DMF (5 ml), ethylbromoacetate (0.04 ml) and potassium carbonate (0.1 g) were added. The reaction mixture was stirred for 16 h at RT. Water and ethyl acetate were added. The organic layer was removed, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography eluting with isohexane:ethyl acetate (1:1) to give the sub-title compound. Yield 0.12 g.

Workup

  1. customThe organic layer was removed
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with isohexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-3a2948816a1b42c9b866d3f940a89ece
Source dataset
uspto-grants-2012_04
Patent number
US08163727B2

Reaction notes

Loading…