Potassium Iodide → 2-Methyl-2-{[4-(2-phenoxy-ethoxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester

HRID 874747Notes

Reaction equation

HRID 874747 reaction equation
[C:1]([O:5][C:6](=[O:23])[C:7]([NH:10][C:11]([C:13]1[CH:21]=[CH:20][C:16]2[S:17][CH:18]=[CH:19][C:15]=2[C:14]=1[OH:22])=[O:12])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[I-].[K+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:9])([NH:10][C:11]([C:13]1[CH:21]=[CH:20][C:16]2[S:17][CH:18]=[CH:19][C:15]=2[C:14]=1[O:22][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 688411722-[(4-Hydroxy-benzo[b]thiophene-5-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester

Product 1

HCID 688422062-Methyl-2-{[4-(2-phenoxy-ethoxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl esterYield 71.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

60 mg 2-[(4-Hydroxy-benzo[b]thiophene-5-carbonyl)-amino]-2-methyl-propionic acid tert-butyl ester, 70 mg cesium carbonate, 36 mg of (2-bromo-ethoxy)-benzene and 6 mg potassium iodide were dissolved in 1 ml of N,N-dimethylformamide and stirred for 2 h at 60° C. 10 ml of ethyl acetate and 10 ml of brine were added to the reaction. The organic layer was separated and washed again with 10 ml of brine. It was then dried over magnesium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by reversed phase HPLC (acetonitrile/water) to afford 58 mg of 2-methyl-2-{[4-(2-phenoxy-ethoxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester.

Workup

  1. customThe organic layer was separated
  2. washwashed again with 10 ml of brine
  3. dry with materialIt was then dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by reversed phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-43dba2c181d04502a790e3c0fae6cff6
Source dataset
uspto-grants-2015_03
Patent number
US08980938B2

Reaction notes

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