Hydrochloric Acid → N-[3-(9-octadecenoyloxy)-11-eicosenoyl]-L-valine

HRID 236483Notes

Reaction equation

HRID 236483 reaction equation
[C:1]([O:20][CH:21]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[CH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:22][C:23]([OH:25])=O)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:43][C@H:44]([C:48]([OH:50])=[O:49])[CH:45]([CH3:47])[CH3:46].[OH-].[Na+].Cl>CN(C)C=O>[C:1]([O:20][CH:21]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[CH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:22][C:23]([NH:43][C@H:44]([C:48]([OH:50])=[O:49])[CH:45]([CH3:47])[CH3:46])=[O:25])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6287L-ValineHCID 14798Sodium HydroxideHCID 536822073-(9-Octadecenoyloxy)-11-eicosenoic acid

Product 1

HCID 54067353N-[3-(9-octadecenoyloxy)-11-eicosenoyl]-L-valineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-hydroxysuccinimide ester of 3-(9-octadecenoyloxy)-11-eicosenoic acid (3 g) in N,N-dimethylformamide (30 ml) was added a solution of L-valine (4.42 g) and a 1N sodium hydroxide solution (37 ml) at 0° C. The resulting mixture was stirred at ambient temperature overnight. The reaction mixture was acidified with 1N hydrochloric acid solution, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give powder of N-[3-(9-octadecenoyloxy)-11-eicosenoyl]-L-valine (2.7 g).

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationEthyl acetate was distilled off

Sources & evidence

ORD record
ord-ad9b9ca8d3a2415da0f5d1c1a4c4e6c9
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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