Methyl chloroformate → N-(Methoxycarbonyl)-L-tert-leucine

HRID 643056Notes

Reaction equation

HRID 643056 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].[OH-].[Na+].Cl[C:13]([O:15][CH3:16])=[O:14]>O1CCOCC1>[CH3:16][O:15][C:13]([NH:1][C@@H:2]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:7]([OH:9])=[O:8])=[O:14]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 164608L-tert-Leucine

Product 1

HCID 11263950N-(Methoxycarbonyl)-L-tert-leucineYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

(L)-tert-Leucine (10 g, 0.076 mol) was dissolved in 1,4-dioxane (40 mL) and treated with 2M NaOH (125 mL, 3.2 equivalents) followed by dropwise addition of methyl chloroformate (11.2 mL, 1.9 equivalents) at 25° C. The mixture was heated at 60° C. for 22 hrs, cooled, and extracted twice with dichloromethane. The aqueous layer was separated, cooled in ice bath, and acidified with 4N HCl (60 mL). The mixture was extracted three times with ethyl acetate, and the organic layer was separated, dried with sodium sulfate, filtered, and the solvents were evaporated to give 14.1 g (98%) of the title compound.

Workup

  1. temperaturecooled
  2. extractionextracted twice with dichloromethane
  3. customThe aqueous layer was separated
  4. temperaturecooled in ice bath
  5. extractionThe mixture was extracted three times with ethyl acetate
  6. customthe organic layer was separated
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were evaporated

Sources & evidence

ORD record
ord-8d6739746dde4cac99c64c2356c0fb39
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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