Trifluoroacetic acid → epsilon-(Benzyloxycarbonyl)-L-lysine

HRID 1757379Notes

Reaction equation

HRID 1757379 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:18](C(NCCCCCCCCCCC)=O)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].FC(F)(F)C(O)=[O:44]>ClCCl>[NH2:1][C@H:2]([C:18]([OH:19])=[O:44])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131719111HCID 131719111, compound

Product 1

HCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 7,2 g of 1j were dissolved in 30 ml of dichloromethane and 15 ml of trifluoroacetic acid were added. The Boc group was immediately removed. After concentration, adding of ether and washing with NaHCO3, the organic phase was dried and concentrated. The Lys(Z) [C(O)NH(CH2)10CH3 ][NH2 ] formed was allowed to reactwith C8F17CH2CH2CO2H (7,6 g, 1,34.10-2 mole); 2.7 g of DCC (1.34.10-2 mole) and 100 mg of HOBT. The peptidiccoupling was carried out in dimethylformamide (DMF). After 24 h the DCU wasfiltered and the product was crystallized.

Workup

  1. customThe Boc group was immediately removed
  2. concentrationAfter concentration
  3. additionadding of ether
  4. washwashing with NaHCO3
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc4b62c4f9274e23b5fa6f0317db1c42
Source dataset
uspto-grants-1995_08
Patent number
US05446023

Reaction notes

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