N-(tert-butoxycarbonyl)glycine → L-Lysine

HRID 904109Notes

Reaction equation

HRID 904109 reaction equation
C([N:8](C(OC(C)(C)C)=O)[C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])C1C=CC=CC=1.C(NCC(O)=O)(OC(C)(C)C)=O>C(Cl)Cl>[NH2:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]

Participants

4

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 22805432HCID 22805432, compound

Product 1

HCID 5962L-Lysine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While maintaining the nitrogen gas atmosphere, three fold molar excess of resin capacity of benzyl-Boc-L-lysine [Lys (Z), Peninsula, supra.] dissolved in methylene chloride is added to the residue of step (B) above. The resulting mixture is shaken and after about 10 minutes, 3 fold molar excess of N,N-dicyclohexylcarbodiimide dissolved in 10-15 ml. of methylene chloride is added with stirring. The resulting mixture is shaken at room temperature for 4.5 to 5 hours. At the end of this period, the reaction mixture is filtered and the residue washed with methylene chloride, ethanol and dried.

Workup

  1. stirringwith stirring
  2. stirringThe resulting mixture is shaken at room temperature for 4.5 to 5 hours
  3. filtrationAt the end of this period, the reaction mixture is filtered
  4. washthe residue washed with methylene chloride, ethanol
  5. customdried

Sources & evidence

ORD record
ord-356d82c72ade4a8188d9ef7bc50d122c
Source dataset
uspto-grants-1980_10
Patent number
US04230696

Reaction notes

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