Methanol → Lys(COOH)NH2

HRID 1826565Notes

Reaction equation

HRID 1826565 reaction equation
C(O[C:9](=[O:27])[C@H:10]([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[NH:11]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.[OH-:28].[Na+].[NH2:30][C@H](C(O)=O)CCCCN.[CH3:40][OH:41]>>[NH2:11][C@H:10]([C:9]([NH2:30])=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:40]([OH:41])=[O:28]

Participants

5

Reactant 4

HCID 887MethanolHCID 5962L-LysineHCID 14798Sodium HydroxideHCID 7408212N2-((Phenylmethoxy)carbonyl)-L-lysine phenylmethyl ester

Product 1

HCID 56607995Lys(COOH)NH2

Procedure

To Nα-CBZ-L-lysine benzyl ester fibrils (113 mg) in methanol (4 ml) was added sodium hydroxide (1 N, 4 ml) and the reaction mixture was stirred overnight. The product Nα-CBZ-L-lysine fibrils was extensively washed with water and methanol and the fibrils were dried under vacuum. To a suspension of Nα-CBZ-L-lysine fibrils (50 mg) in acetonitrile (4 ml) was added trimethyl silyl iodide (1 ml). The mixture was stirred for 3 hours at 40° C. The final bifunctional fibrils were extensively washed with water, methanol, 0.5 N sodium hydroxide, acetonitrile and methylene chloride. Amino acid analysis showed 0.3 μmols lysine per gram of fibrils.

Workup

  1. washThe product Nα-CBZ-L-lysine fibrils was extensively washed with water and methanol
  2. customthe fibrils were dried under vacuum
  3. additionTo a suspension of Nα-CBZ-L-lysine fibrils (50 mg) in acetonitrile (4 ml)
  4. additionwas added trimethyl silyl iodide (1 ml)
  5. stirringThe mixture was stirred for 3 hours at 40° C
  6. washThe final bifunctional fibrils were extensively washed with water, methanol, 0.5 N sodium hydroxide, acetonitrile and methylene chloride

Sources & evidence

ORD record
ord-341f1af052464b4d9a1b77f58532fb8f
Source dataset
uspto-grants-2006_05
Patent number
US07052861B2

Reaction notes

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