Methanol → (2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acid

HRID 1704292Notes

Reaction equation

HRID 1704292 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[C:12](=O)([O:18]N1C(=O)CCC1=O)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].CO>O.[OH-].[K+]>[C:14]([O:13][C:12]([NH:8][CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]([C:9]([OH:11])=[O:10])[NH2:2])=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 69568L-Lysine monohydrochlorideHCID 83168Carbonic acid, 1,1-dimethylethyl 2,5-dioxo-1-pyrrolidinyl ester

Product 1

HCID 2733283(2S)-2-amino-6-(((tert-butoxy)carbonyl)amino)hexanoic acidYield 71.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

To the solution of 575 mg of lysine monohydrochloride in 2 ml of water, 6.2 ml of 1N methanolic potassium hydroxide was added and then 645 mg of t-butyl succinimidyl carbonate in 3 portions was mixed in over 20 minutes while stirring at room temperature. Stirring was continued for another 2 hours, then the reaction mixture was acidified to pH 5, methanol evaporated and the white precipitate collected by filtration giving 779 mg (quantitative yield) of the crude title compound. This was twice recrystallized from warm water to give 529.7 mg (68%) of pure compound.

Workup

  1. stirringStirring
  2. customevaporated
  3. filtrationthe white precipitate collected by filtration
  4. customgiving 779 mg (quantitative yield) of the crude title compound
  5. customThis was twice recrystallized
  6. temperaturefrom warm water

Sources & evidence

ORD record
ord-7bf86a523b32455db5430f2213b14924
Source dataset
uspto-grants-1978_11
Patent number
US04126628

Reaction notes

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