Ethanol → ethyl Nalpha-benzyloxycarbonyl-L-lysinate

HRID 1982366Notes

Reaction equation

HRID 1982366 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](O)[CH3:22].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

Product 1

HCID 13851264ethyl Nalpha-benzyloxycarbonyl-L-lysinateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing 29.9 gm (0.107 mol) of Nα-benzyloxycarbonyl-L-lysine, 30 ml of ethanol, and 9.0 ml of concentrated sulfuric acid in 250 ml of methylene chloride was refluxed for 22.5 hours. The reaction mixture was then cooled to room temperature and basified to pH of about 13 by the careful addition of a saturated aqueous solution of potassium carbonate. The aqueous phase was removed and the organic phase was washed one more time with a saturated potassium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to give 29.8 gm (91%) of ethyl Nα-benzyloxycarbonyl-L-lysinate (II-F) as an oil.

Workup

  1. temperaturewas refluxed for 22.5 hours
  2. customThe aqueous phase was removed
  3. washthe organic phase was washed one more time with a saturated potassium carbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fb0e7fdbadd4857b7c56278f95eafb2
Source dataset
uspto-grants-1986_06
Patent number
US04596791

Reaction notes

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