Hydrochloric Acid → N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonine

HRID 868221Notes

Reaction equation

HRID 868221 reaction equation
[CH2:1](/[C:3](=[CH:16]\[CH3:17])/[CH:4]=[CH:5]/[C:6]([O:8]N1C(=O)CCC1=O)=O)[CH3:2].[NH2:18][C@H:19]([C:23]([OH:25])=[O:24])[C@@H:20]([CH3:22])[OH:21].C(N(CC)CC)C.Cl>O1CCCC1.CN(C)C=O.O>[CH2:1](/[C:3](=[CH:16]\[CH3:17])/[CH:4]=[CH:5]/[C:6]([NH:18][C@H:19]([C:23]([OH:25])=[O:24])[C@@H:20]([CH3:22])[OH:21])=[O:8])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6288L-ThreonineHCID 8471TriethylamineHCID 14329790N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide

Product 1

HCID 86742403N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonineYield 52.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide (1.19 g) in a mixture of tetrahydrofuran (50 ml) and dimethylformamide (30 ml) was added a solution of L-threonine (2.38 g) and triethylamine (2.78 ml) in water (50 ml). The mixture was stirred at ambient temperature for 6 hours and then acidified with 1N hydrochloric acid. The resulting mixture was extracted with ethyl acetate, washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give N-[(E,E)-4-ethyl-2,4-hexadienoyl]-L-threonine (640 mg).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0288beae36d2428cb8c749352d91a34f
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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