Ethyl trifluoroacetate → 2-N-trifluoroacetyl-6-N-benzyloxycarbonyl-lysine

HRID 478118Notes

Reaction equation

HRID 478118 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([C:18]([OH:20])=[O:19])[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:23][C:24](=O)[C:25]([F:28])([F:27])[F:26])C>C(O)C>[F:26][C:25]([F:28])([F:27])[C:24]([NH:17][C@H:16]([C:18]([OH:20])=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[O:23]

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysine

Product 1

HCID 865853332-N-trifluoroacetyl-6-N-benzyloxycarbonyl-lysine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

100.0 g (356.7 mmol) of 6-N-benzyloxycarbonyl-L-lysine is dissolved in a mixture that consists of 1000 ml of trifluoroacetic acid ethyl ester and 500 ml of ethanol, and it is stirred for 24 hours at room temperature. It is evaporated to the dry state, and the residue is crystallized from diisopropyl ether.

Workup

  1. customIt is evaporated to the dry state
  2. customthe residue is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-aee2460350b940a696b357cf09080bc7
Source dataset
uspto-grants-2003_11
Patent number
US06641797B2

Reaction notes

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