L-Isoleucine → tert-Butoxycarbonyl-L-isoleucine

HRID 2082975Notes

Reaction equation

HRID 2082975 reaction equation
[C:1]([O:5][C:6]([O:8]N=C(C(OCC)=O)C(OCC)=O)=O)([CH3:4])([CH3:3])[CH3:2].[NH2:21][C@H:22]([C:27]([OH:29])=[O:28])[C@H:23]([CH2:25][CH3:26])[CH3:24].[OH-].[Na+]>C(O)(C)(C)C>[C:1]([O:5][C:6]([NH:21][C@H:22]([C:27]([OH:29])=[O:28])[C@H:23]([CH2:25][CH3:26])[CH3:24])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6306L-IsoleucineHCID 14798Sodium HydroxideHCID 13240888HCID 13240888, compound

Product 1

HCID 2724762tert-Butoxycarbonyl-L-isoleucineYield 103.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of diethyl 2-tert-butoxycarbonyloxyiminomalonate (1.9 g.) in tert-butyl alcohol (5 ml.) was added to a solution of L-isoleucine (656 mg.) in a 1N sodium hydroxide aqueous solution (5.0 ml.). The mixture was stirred for 3 hours at room temperature. The tert-Butyl alcohol was removed from the reaction mixture under reduced pressure and water was added to the residue. The mixture was washed with ether, adjusted to pH 3 with a 5% citric acid aqueous solution and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to give N-tert-butoxycarbonyl-L-isoleucine (1.2 g.), oil.

Workup

  1. customThe tert-Butyl alcohol was removed from the reaction mixture under reduced pressure and water
  2. additionwas added to the residue
  3. washThe mixture was washed with ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8b27315523314e77aeb3405837242842
Source dataset
uspto-grants-1978_04
Patent number
US04083848

Reaction notes

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