Dimethylformamide → methyl (2S)-3-[4-(2-methoxyethoxymethoxy)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

HRID 5726

Reaction equation

HRID 5726 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].[Na+].CN(C)[CH:26]=[O:27]>O1CCCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:1][O:2][CH2:3][CH2:4][O:27][CH3:26])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 7019130Boc-Tyr-OMe

Product 1

HCID 53880497methyl (2S)-3-[4-(2-methoxyethoxymethoxy)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.39 g of N-tert-butoxycarbonyltyrosine methyl ester was dissolved in 65 ml of tetrahydrofuran and 65 ml of dimethylformamide, and to the solution was added 1.9 g of 60% sodium hydride with stirring in an ice bath. After removing from the ice bath, the mixture was stirred at a room temperature for 30 minutes, and after addition of 5.4 g of methoxyethoxymethyl chloride with ice cooling, stirred for 15 hours allowing to warm to a room temperature. The reaction mixture was poured on ice, saturated with sodium chloride and extracted twice with 800 ml of chloroform. The extract was dried over magnesium sulfate and the solvent was evaporated under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with hexane/ethyl acetate (4:1) to obtain 13.85 g of the title compound in a colorless amorphous form.

Workup

  1. customAfter removing from the ice bath
  2. stirringthe mixture was stirred at a room temperature for 30 minutes
  3. additionafter addition of 5.4 g of methoxyethoxymethyl chloride with ice cooling
  4. stirringstirred for 15 hours
  5. additionThe reaction mixture was poured on ice, saturated with sodium chloride
  6. extractionextracted twice with 800 ml of chloroform
  7. dry with materialThe extract was dried over magnesium sulfate
  8. customthe solvent was evaporated under a reduced pressure
  9. customresulting residue
  10. washeluted with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4e42a8b5fe4a46378087c9d3b246d21a
Source dataset
uspto-grants-1993_09
Patent number
US05245034

Linked notes

Loading…