Реакция #87141

Уравнение реакции

glycine

anisaldehyde

KOH

→

2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

Выход 23.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   КонцентрированиеThe mixture was concentrated under vacuum the majority of ethanol
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water (800 mL)
3. 3
   ПромывкаThe resulting mixture was washed with EtOAc (200 mL×2)
4. 4
   Другоеto remove any impurities
5. 5
   КонцентрированиеThe aqueous layer was concentrated to a volume of ˜400 mL
6. 6
   ФильтрацияThe mixture was filtered
7. 7
   Промывкаthe filtration cake was washed thoroughly with water (100 mL×2)
8. 8
   Другоеdried

Методика

A solution of glycine (45 g, 0.60 mol) and anisaldehyde (122 g, 0.900 mol) in ethanol (1.5 L) was stirred at ambient temperature and KOH (82.7 g, 1.47 mol) was added. The reaction mixture was stirred overnight at ambient temperature. The mixture was concentrated under vacuum the majority of ethanol. The residue was dissolved in water (800 mL) and the solution was adjusted to pH=5 with 4 N aqueous HCl. The resulting mixture was washed with EtOAc (200 mL×2) to remove any impurities. The aqueous layer was concentrated to a volume of ˜400 mL. The mixture was filtered and the filtration cake was washed thoroughly with water (100 mL×2) and dried to afford 2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (29 g, 23% yield, threo-) as a colorless solid.

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