Dimethylformamide → HCID 90060119, compound

HRID 1779154Notes

Reaction equation

HRID 1779154 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22](=O)([O-])[O-:23].[K+].[K+].I[CH2:29][CH2:30][CH2:31][CH3:32].CN([CH:36]=[O:37])C>C(OCC)(=O)C>[CH3:22][O:23][CH2:31][CH2:32][C:36](=[O:37])[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7].[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 7019130Boc-Tyr-OMe

Product 2

HCID 90060040Tert-butyl 4-methoxy-2-oxobutanoateHCID 90060119HCID 90060119, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Commercially available (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate (12 g, 40.63 mmol, 1 eq.) was dissolved in dehydrated DMF (30 mL), and potassium carbonate (6.177 g, 44.695 mmol, 1.1 eq.) and 1-iodobutane (5.55 mL, 48.756 mmol, 1.2 eq.) were added to the solution, which was stirred at 40° C. for a whole day and night and cooled to room temperature. The mixture was diluted with ethyl acetate, washed 3 times with water, and then with a saturated aqueous solution of ammonium chloride, and dried over anhydrous sodium sulfate. The organic layer was filtered and the solvent was distilled off. The residue was purified by aminosilica gel column chromatography (by elution with dichloromethane) to obtain the desired compound, (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-butoxyphenyl)propanoate as a white solid (11.842 g, 83% yield).

Workup

  1. temperaturecooled to room temperature
  2. washwashed 3 times with water
  3. dry with materialwith a saturated aqueous solution of ammonium chloride, and dried over anhydrous sodium sulfate
  4. filtrationThe organic layer was filtered
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by aminosilica gel column chromatography (by elution with dichloromethane)

Sources & evidence

ORD record
ord-5e74c83f2bb44c8ea714138785c62e41
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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