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

HRID 35573

反応式

HRID 35573 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7f5eeb8f4a4e4cc5a67cdfebe04fa304
出典データセット
uspto-grants-1988_08
特許番号
US04767768

関連ノート

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