L-Valine → Boc-L-Valine

HRID 2248036Notes

Reaction equation

HRID 2248036 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[C:9]([O:13][C:14](=O)[O:15]C(C)(C)C)([CH3:12])([CH3:11])[CH3:10]>O1CCOCC1.O>[NH:1]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 6287L-ValineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 83693Boc-L-Valine

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 10 g (0.086 mol) of valine and 3.4 g (0.086 mol) of NaDH in 250 ml of dioxan: H2O (2:1) mixture was slowly added 20.5 g (0.094 mol) of ditertbutylcarbonate at 0° C. with vigorous stirring. The reaction mixture was then stirred for another hour at room temperature, dioxan was removed under reduced pressure, and BOC-Val-OH was obtained by acidifying the mixture to a pH of 2-3. The raw product consisting of 18 g of viscous oil was obtained after evaporating the solvent from the ethyl acetate extracts.

Workup

  1. customat 0° C.
  2. customdioxan was removed under reduced pressure

Sources & evidence

ORD record
ord-4def40c5bf8548508722189367ba103c
Source dataset
uspto-grants-1991_08
Patent number
US05037883

Reaction notes

Loading…