Ethyl bromoacetate → HCID 68554790, compound

HRID 1967580Notes

Reaction equation

HRID 1967580 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]([CH2:25][CH3:26])[CH3:24])[CH:16]=2)=[C:9]([Cl:27])[CH:8]=1)[CH3:2].Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([CH:23]([CH2:25][CH3:26])[CH3:24])[CH:16]=2)=[C:9]([Cl:27])[CH:8]=1)[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH3:2]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 68557314HCID 68557314, compound

Product 1

HCID 68554790HCID 68554790, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To [4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenylamino]-acetic acid ethyl ester (Example 2, step 2) (48.0 g, 0.11 mol), ethyl bromoacetate (188 g, 1.12 mol) and diisopropylethylamine (145.57 g, 1.12 mol) in DMF (480 mL) were stirred at 120° C. for 18 h. The reaction mixture was poured in to ice-water. The product was taken up in ethyl acetate, washed with water, brine, dried over sodium sulphate, filtered and concentrated to give the crude product, which was purified by column chromatography over flash silica gel (hexane:ethyl acetate 90:10) to give pure {[4-(3-sec-Butyl-4-methoxy-phenoxy)-3,5-dichloro-phenyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester (27.1 g, 47% yield).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography over flash silica gel (hexane:ethyl acetate 90:10)

Sources & evidence

ORD record
ord-0d1dcf4c967f4f3c988de1194716837a
Source dataset
uspto-grants-2013_04
Patent number
US08420851B2

Reaction notes

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