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

HRID 35573
Notes
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Reaction equation

HRID 35573 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 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-7f5eeb8f4a4e4cc5a67cdfebe04fa304
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04767768

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes