Potassium Carbonate → HCID 68428986, compound

HRID 642557Notes

Reaction equation

HRID 642557 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:7]=1[CH2:15]Br)=[O:5])[CH3:2].[CH2:17]([O:19][C:20](=[O:34])[CH2:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:8][C:7]=1[CH2:15][N:22]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][CH3:33])[CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:34])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19895532Ethyl 2-(2,4-dimethoxybenzylamino)acetateHCID 68428723HCID 68428723, compound

Product 1

HCID 68428986HCID 68428986, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A portion of the crude 4-bromomethyl-2-tert-butyl-thiazole-5-carboxylic acid ethyl ester (12.6 g, 41.0 mmol), N-(2,4-dimethoxy-benzyl)glycine ethyl ester (11.6 g, 41.0 mmol), and potassium carbonate (6.2 g, 45 mmol) in 100 ml of anhydrous DMF was stirred for 18 h. The mixture was partitioned into a biphasic water-ethyl acetate mixture and the isolated organic layer was then washed with brine, dried over anhydrous magnesium sulfate, concentrated to a residue, and purified by flash chromatography: eluting the desired product from silica gel with a gradient of 10-35% ethyl acetate in hexanes. 13 g of a yellow oil was isolated. MS (ESI+): 479.4 (M+1).

Workup

  1. customThe mixture was partitioned into a biphasic water-ethyl acetate mixture
  2. washthe isolated organic layer was then washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated to a residue
  5. custompurified by flash chromatography
  6. washeluting the desired product from silica gel with a gradient of 10-35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8ea4fbe6f724422a90fda01787d2ca73
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

Loading…