L-Isoleucine → tert-Butoxycarbonyl-L-isoleucine

HRID 596207Notes

Reaction equation

HRID 596207 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.), and the mixture was stirred for 3 hours at room temperature. 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. customtert-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-66c92f9177d84b878df44fda7d3303ee
Source dataset
uspto-grants-1977_03
Patent number
US04010178

Reaction notes

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