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

HRID 2226575노트

반응식

HRID 2226575 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(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).

후처리

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

출처 및 근거

ORD 기록
ord-d5a2eae0dd0145f8a3bf7310978c8aea
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348978

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