Ethyl bromoacetate → HCID 18408639, compound

HRID 896750Notes

Reaction equation

HRID 896750 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:19]2[CH:24]=[C:23]([O:25][CH2:26][CH3:27])[C:22]([O:28][CH2:29][CH3:30])=[CH:21][C:20]=2[OH:31])[CH2:11][NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[CH:5][CH:4]=1)#[N:2].C(=O)(O)[O-].[K+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C)C=O>[CH2:42]([O:41][C:39](=[O:40])[CH2:38][O:31][C:20]1[CH:21]=[C:22]([O:28][CH2:29][CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[CH:24][C:19]=1[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:11][NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])[CH3:43]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 516893Potassium BicarbonateHCID 22890469HCID 22890469, compound

Product 1

HCID 18408639HCID 18408639, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propane-1-sulfonic acid [2-(4-cyano-phenylamino)-2-(4,5-diethoxy-2-hydroxy-phenyl)-ethyl]-amide (100 mg, 0.223 mmoles) was dissolved in dimethylformamide (1.5 ml) and treated with solid potassium bicarbonate (22 mg, 0.223 mmoles) followed by ethyl bromoacetate (0.37 ml, 0.223 mmoles). The reaction was stirred under N2, for 67 hours. Thin-layer chromatography showed presence of a new product with a higher Rf. The reaction was quenched in water and extracted with ethyl acetate. The ethyl acetate extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The residue was submitted to flash chromatography (ethyl acetate:methylene chloride 1:9) to yield 78 mg of {2-[1-(4-cyano-phenylamino)-2-(propane-1-sulfonylamino)-ethyl]-4,5-diethoxy-phenoxy}-acetic acid ethyl ester. 1HNMR (CHCl3): 7.35 (d, 2H), 6.81 (s, 1H), 6.57 (d, 2H), 6.43 (s, 1H), 4.81 (t, 1H), 4.68 (ABq, 2H), 4.56 (t, 1H), 4.26 (q, 2H), 4.05 (q, 2H), 3.95 (m, 2H), 3.54 (t, 2H), 2.98 (m, 2H) 1.80 (m, 2H) 1.42 (t, 3H), 1.32 (t, 6H), 1.02 (t, 3H). MS (M+H): 534.

Workup

  1. customThe reaction was quenched in water
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-82aa485b1a414dcfa4b5e437b4547997
Source dataset
uspto-grants-2005_07
Patent number
US06919369B2

Reaction notes

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