Dimethylformamide → Methyl-2-[(t-butoxycarbonyl)amino]-3-[-(4-formylphenoxy) phenyl]propanoate

HRID 1007283Notes

Reaction equation

HRID 1007283 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:23])[CH:6]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1.F[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1.CN(C=[O:37])C>>[CH3:3][O:4][C:5](=[O:23])[CH:6]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:37][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 4459028Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 22669057Methyl-2-[(t-butoxycarbonyl)amino]-3-[-(4-formylphenoxy) phenyl]propanoateYield 85%

Conditions

Temperature
80 °C

Procedure

To a suspension of fresh sodium hydride (0.813 g, 33.9 mmol) in dry DMF (20 ml) under nitrogen atmosphere was added the solution of methyl-2-[(t-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (10 g, 33.9 mmol) in DMF (20 ml) slowly. The mixture was stirred for 15 minutes. 4-Fluorobenzaldehyde (4.20 g, 33.9 mmol) was added and the mixture was heated to 80° C. After completion of the reaction, the solvent was removed by high vacuum and the mixture was quenched with addition of saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3×50 ml). After washing with brine and dried on anhydrous sodium sulfate, the solvent was evaporated and the product was purified with flash column from eluent of hexanes: ethyl ether; 12/30 to 12/22 to afford the title compound as an oil (yield 11.5 g, 85.0%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by high vacuum
  3. customthe mixture was quenched with addition of saturated aqueous ammonium chloride
  4. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  5. washAfter washing with brine
  6. dry with materialdried on anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customthe product was purified with flash column from eluent of hexanes

Sources & evidence

ORD record
ord-20903513c1ef421cb45a4945af91f8d9
Source dataset
uspto-grants-2004_09
Patent number
US06794401B2

Reaction notes

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