Hydrochloric Acid → N-(z-15-tetracosenoyl)-L-threonine

HRID 968095Notes

Reaction equation

HRID 968095 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4].C(=O)(O)[O-].[Na+].[C:14](ON1C(=O)CCC1=O)(=[O:38])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].Cl>O.C(COC)OC.CCCCCC.C(OCC)C.C(O)(=O)C>[C:14]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[C@@H:3]([CH3:5])[OH:4])(=[O:38])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 516892Sodium BicarbonateHCID 45040426HCID 45040426, compound

Product 1

HCID 86595255N-(z-15-tetracosenoyl)-L-threonine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 21924843Hexane ether acetic acidSolvent

Procedure

A mixture of L-threonine (5 mmol, 0.595 g), sodium bicarbonate (5 mmol, 0.420 g) and succinimidyl nervonate (5 mmol, 2.320 g, prepared according to Example 1A) in water (2 mL) and dimethoxyethane (5 mL) were refluxed for 2 hours until no ester remained according to TLC (hexane-diethyl ether-acetic acid, 80:18:2). Acidification to pH 2 with concentrated hydrochloric acid and chilling gave the title product, which was washed with water, dried and crystallised from chloroform. It was finally washed with hexane to remove small amounts of non-polar contaminants.

Sources & evidence

ORD record
ord-64e3691902a44fcbb9108759e9b6f9f9
Source dataset
uspto-grants-2005_10
Patent number
US06956059B2

Reaction notes

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