Potassium Carbonate → HCID 59608440, compound

HRID 2067160Notes

Reaction equation

HRID 2067160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([NH:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=1>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=2)=[CH:4][C:3]=1[C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1)=[O:10]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 40672073-Methoxybenzyl bromideHCID 59608423HCID 59608423, compound

Product 1

HCID 59608440HCID 59608440, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 4-({[(2-chloro-5-hydroxyphenyl)carbonyl]amino}methyl)benzoate (95 mg, 0.3 mol), potassium carbonate (2 eq, 83 mg, 0.6 mmol) and 1-(bromomethyl)-3-(methyloxy)benzene (1.2 eq, 50 ul, 0.36 mmol) in DMF (2 ml) was stirred at room temperature for 2 hours. The mixture was then diluted with ethyl acetate (100 ml) and H2O (80 ml). Layers separated, organic layer washed with brine (80 ml) then dried and evaporated in vacuo. Residue purified by column chromatography (Biotage SP4) eluting with 0-40% ethylacetate in hexanes to give the title compound as a clear oil. MS (ES+) m/z 440 [M+H]+ (C24H2235ClNO5). 1H-NMR (400 MHz, d6-DMSO) δ 3.76 (3H, s), 3.85 (3H, s), 4.51 (2H, d, J 6), 5.12 (2H, s), 6.89-7.96 (11H, m), 7.46 (2H, d, J 8.4), 7.92 (2H, m), 9.05 (1H, J 6).

Workup

  1. customLayers separated
  2. washorganic layer washed with brine (80 ml)
  3. customthen dried
  4. customevaporated in vacuo
  5. customResidue purified by column chromatography (Biotage SP4)
  6. washeluting with 0-40% ethylacetate in hexanes

Sources & evidence

ORD record
ord-0cecb052aa5045c9ba79065da1466a4f
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

Loading…