N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine synthesis
- Product Name:N-(tert-buloxycarbonyl)-3,4-dihydroxy-L-phenylalanine
- CAS Number:30033-24-0
- Molecular formula:C14H19NO6
- Molecular Weight:297.3
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Yield: 100%
Reaction Conditions:
with sodium hydroxide in 1,4-dioxane;water at 20;
Steps:
1.a
To a solution of 5.004 g (25.4 mmol) L-Dopa (1) in 40 ml dioxane and 25 ml H2O,28 ml (28 mmol) 1 M NaOH and 6.0893 g (27.9 mmol) BOC2O dissolved in 8 ml dioxane was added. The resulting solution was stirred at r.t. After 30 minutes the pH was adjusted to 10 by the addition of 1 M NaOH. The pH was again adjusted to 10 after 1 h and after 7.5 h. After the last pH adjustment the solution was stirred overnight. The volatiles were evaporated and resulting water phase was the adjusted to pH 2 and extracted with 3x100 ml EtOAc. The pooled organic phases were washed with 150 ml water, 150 ml brine, dried over Na2SO4, filtered and evaporated to give 7.6 g (25.4 mmol, 100 %) Λ/-Boc-protected L-Dopa (2).
References:
ONCOREL AB;PERSSON, Jenny;LARSSON, Rikard;STERNER, Olov;JOHANSSON, Martin WO2010/149943, 2010, A1 Location in patent:Page/Page column 31
24424-99-5
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30033-24-0
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