L-Methionine → N-(z-15-tetracosenoyl)-L-methionine

HRID 968094Notes

Reaction equation

HRID 968094 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].C(N(CC)CC)C.[C:17](ON1C(=O)CCC1=O)(=[O:41])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].CCCCCC.C(OCC)C.C(O)(=O)C>O.CC(C)=O>[C:17]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])(=[O:41])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

6

Reactant 4

HCID 6137L-MethionineHCID 8471TriethylamineHCID 21924843Hexane ether acetic acidHCID 45040426HCID 45040426, compound

Product 1

HCID 86595254N-(z-15-tetracosenoyl)-L-methionine

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred solution of L-methionine (5 mmol, 0.75 g) and triethylamine (15 mmol, 2.1 mL) in 15 mL of water-acetone (1:1), was added succinimidyl nervonate (5 mmol, 2.32 g, prepared according to Example 1A) in portions. The mixture was stirred for 4 hours until no ester remained according to TLC (hexane-diethyl ether-acetic acid, 80:18:2). The solvents were evaporated under reduced pressure. 10 mL of water was then added and the mixture was acidified with concentrated hydrochloric acid to pH 2. The precipitated product was separated by filtration, washed with water and crystallised from ethanol. Hexane was then used to remove traces of non-polar impurities from the title compound.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. addition10 mL of water was then added
  3. customThe precipitated product was separated by filtration
  4. washwashed with water
  5. customcrystallised from ethanol
  6. customto remove traces of non-polar impurities from the title compound

Sources & evidence

ORD record
ord-16d8ea989aea4684a1c585165351a7a1
Source dataset
uspto-grants-2005_10
Patent number
US06956059B2

Reaction notes

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