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

HRID 35573

반응식

HRID 35573 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7f5eeb8f4a4e4cc5a67cdfebe04fa304
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767768

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