L-Isoleucine → HCID 86599729, compound

HRID 643057Notes

Reaction equation

HRID 643057 reaction equation
[NH2:1][C@H:2](C(O)=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[OH-:10].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14].[O:17]1[CH2:22][CH2:21]OCC1>>[CH3:16][O:15][C:13]([NH:1][C@H:2]([C@@H:3]([CH3:4])[CH2:5][CH3:6])[CH2:21][C:22]([OH:17])=[O:10])=[O:14]

Participants

5

Reactant 4

HCID 6306L-IsoleucineHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 312751,4-Dioxane

Product 1

HCID 86599729HCID 86599729, compoundYield 80%

Procedure

(L)-isoleucine (7.43 g, 57 mmol) was dissolved in dioxane (28 mL) and treated with 2N sodium hydroxide (93.5 mL, 3.3 equivalents) and methyl chloroformate (8.75 mL, 2 equivalents) at 60° C. for 16 hrs. The mixture was extracted with dichloromethane (2×). The mixture made acidic with 4N HCl, and extracted with ethyl acetate (3×), dried over sodium sulfate, filtered and the solvents were evaporated to give 8.6 g (80%) of the title compound.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×)
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-e608ca0bb55246128c1908991c413235
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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