Hydrochloric Acid → 2(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid

HRID 2226575ノート

反応式

HRID 2226575 の反応式
[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26].C(N(CC)CC)C.Cl>O1CCCC1>[C:1]([S:4][CH2:5][C@@H:6]([CH3:10])[C:7](=[O:9])[O:8][C@@H:24]([CH2:28][S:29][CH3:30])[C:25]([OH:27])=[O:26])(=[O:3])[CH3:2]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2724506D-beta-acetylthioisobutyric acidHCID 15647666(R)-2-hydroxy-3-(methylthio)propanoic acid

生成物 1

HCID 102656742(R)-(3-(Acetylthio)-2(S)-methyl-1-oxopropoxy)-3-(methylthio)propanoic acid収率 15.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

(S)-3-(Acetylthio)-2-methylpropanoic acid (0.38 g, 2.35 mmol) and 1,1'-carbonyldiimidazole (0.38 g, 2.35 mmol) were stirred under nitrogen, in tetrahydrofuran (10 ml). After 30 min, a solution of (R)-2-hydroxy-3-(methylthio)propanoic acid (0.32 g, 2.35 mmol), triethylamine (0.33 ml, 2.35 mmol) and tetrahydrofuran (10 ml) was added dropwise. The reaction mixture was stirred at 25° for 18 h before evaporation of the solvent. The residue was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic extracts were dried (Na2SO4) and the solvent evaporated. Chromatography on silica with dichloromethane/ethyl acetate as eluant gave the sub-title compound (0.1 g).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. customthe solvent evaporated

出典と根拠

ORDレコード
ord-d5a2eae0dd0145f8a3bf7310978c8aea
出典データセット
uspto-grants-1994_09
特許番号
US05348978

反応ノート

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