Tetrahydrofuran → ethyl N-(diphenylmethylidene)-3-methoxyphenylalaninate

HRID 1972544Notes

Reaction equation

HRID 1972544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Br.[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].C1COCC1>O>[C:11]1([C:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:18][C@H:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 86670395ethyl N-(diphenylmethylidene)-3-methoxyphenylalaninateYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100-mL round-bottomed flask was added 3-methoxybenzyl bromide (0.73 mL, 5.22 mmol, Sigma-Aldrich, St. Louis, Mo.), ethyl N-(diphenylmethylene)glycinate (1.40 g, 5.22 mmol, Acros, Pittsburgh, Pa.), 5 M sodium hydroxide (5.22 mL, 26.1 mmol) and THF (20 mL). The reaction mixture was stirred at room temperature for 2 d. After that time, the mixture was diluted with water (30 mL) and extracted with EtOAc (2×60 mL). The organic extracts were washed with saturated NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. Purification by silica gel chromatography, eluting with 20% EtOAc in hexanes gave ethyl N-(diphenylmethylidene)-3-methoxyphenylalaninate (1.56 g).

Workup

  1. extractionextracted with EtOAc (2×60 mL)
  2. washThe organic extracts were washed with saturated NaCl (30 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto give the crude material as light-yellow oil
  7. customPurification by silica gel chromatography
  8. washeluting with 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-27d52f642abc46e58976e96ab6821635
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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