1,2-Dichloroethane → L-Lysine

HRID 987885Notes

Reaction equation

HRID 987885 reaction equation
[CH2:1](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C([NH:22][C@H:23]([C:33]([OH:35])=[O:34])[CH2:24]OCC1C=CC=CC=1)(OC(C)(C)C)=O.C([N:38]([CH2:41][CH3:42])CC)C>CN(C=O)C.ClCCl>[NH2:22][C@H:23]([C:33]([OH:35])=[O:34])[CH2:24][CH2:1][CH2:42][CH2:41][NH2:38]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 5962L-Lysine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of EDC (8.0 g, 41,73 mmol), HOBt (5.63 g, 41.73 mmol), N-BOC-(O-benzyl)-L-serine (12.45 g, 41.73 mmol) was stirred in DMF (300 mL) at room temperature for 2 hours. To this reaction mixture was added N-ε-(carbobenzoxy)-L-lysine-, methyl ester hydrochloride (13.80 g, 41.73 mmol), followed by triethylamine (5.81 mL), and the stirring was continued for 18 hours. The mixture was dissolved in dichloromethane (1 L), and the organic phase was washed with dilute hydrochloric acid (1N, 500 mL), saturated sodium bicarbonate (500 mL), and brine. The organic layer was dried (MgSO4), filtered, and concentrated to afford 23 g of L-lysine, [N-ε-(carbobenzoxy)]-N-α-[L-[N-BOC-(O-benzyl)seryl]]-, methyl ester.

Workup

  1. washthe organic phase was washed with dilute hydrochloric acid (1N, 500 mL), saturated sodium bicarbonate (500 mL), and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-539d730c1d2b459ebf67bcca18eb0991
Source dataset
uspto-grants-2003_10
Patent number
US06632921B1

Reaction notes

Loading…