epsilon-(Benzyloxycarbonyl)-L-lysine → Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysine

HRID 236505Notes

Reaction equation

HRID 236505 reaction equation
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH2:39]([O:46][C:47]([NH:49][CH2:50][CH2:51][CH2:52][CH2:53][C@@H:54]([C:56]([OH:58])=[O:57])[NH2:55])=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C)C=O.[OH-].[Na+]>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:55][C@H:54]([C:56]([OH:58])=[O:57])[CH2:53][CH2:52][CH2:51][CH2:50][NH:49][C:47]([O:46][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:48])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 1715626epsilon-(Benzyloxycarbonyl)-L-lysineHCID 134890283-Hexadecanoyloxyoctadecanoic acid

Product 1

HCID 70533277Nalpha-(3-hexadecanoyloxyoctadecanoyl)-Nepsilon-benzyloxycarbonyl-L-lysineYield 76.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (7.5 g) prepared by the method of Example 8 (1) in dimethylformamide (200 ml) was added a solution of Nε -benzyloxycarbonyl-L-lysine (6.6 g) in 1N sodium hydroxide (23.6 ml) at room temperature. The mixture was stirred at ambient temperature for 3 hours. The precipitated solid was collected by filtration and the filtrate was concentrated under reduced pressure. The solid and the residue was combined. Then, the mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water. The ethyl acetate solution was dried over magnesium sulfate, and then concentrated to give a residue which was dried up by high vacuum pump to afford powder of Nα -(3-hexadecanoyloxyoctadecanoyl)-Nε -benzyloxycarbonyl-L-lysine (8.5 g).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a residue which
  8. customwas dried up by high vacuum pump

Sources & evidence

ORD record
ord-b110d253cd59422cb35bb93ee2b2fcbf
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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