1,2-Dichloroethane → L-Lysine

HRID 1586246Notes

Reaction equation

HRID 1586246 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.CN(C=O)C.C([N:43]([CH2:46][CH3:47])CC)C>ClCCl>[NH2:22][C@H:23]([C:33]([OH:35])=[O:34])[CH2:24][CH2:1][CH2:47][CH2:46][NH2:43]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 5962L-Lysine

Reagents, catalysts & solvents 1

HCID 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-(carbo-benzoxy)-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-b60689d60d034e9383071de54143bb4b
Source dataset
uspto-grants-1999_08
Patent number
US05942600

Reaction notes

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