Potassium Carbonate → 2-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid

HRID 732064노트

반응식

HRID 732064 반응식
Cl[C@H:2]([CH3:6])[C:3]([OH:5])=[O:4].[CH3:7][N:8]1[C:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:10]=[C:9]1[SH:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CN(C=O)C>[CH3:7][N:8]1[C:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:10]=[C:9]1[S:18][CH:2]([CH3:6])[C:3]([OH:5])=[O:4]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27245402-Chloropropionic acid, (+)-HCID 178481692HCID 178481692, 화합물

생성물 1

HCID 177434532-(4-Methyl-5-thiophen-2-yl-4H-[1,2,4]triazol-3-ylsulfanyl)-propionic acid수율 12.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

(R)-2-chloro-propionic acid (500 mg, 4.6 mmol), 4-methyl-5-thiophen-2-yl-4H-[1,2,4]triazole-3-thiol (1.09 g, 5.58 mmol) and potassium carbonate (1.94 g, 14.03 mmol) were dissolved in acetonitrile (15 ml) at room temperature. Reaction proceeded for 2.5 h and was partitioned between ethyl acetate (350 ml) and water 3 times, washed with 1 M HCl, once with saturated brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. Reaction was not completed at this stage and the crude was stirred in DMF (10 ml) overnight. Extraction was repeated and purification was performed by SPE (solid phase extraction) chromatography on silica gel using 300 ml ethyl acetate, 100 ml 1%, and 100 ml 3% formic acid in ethyl acetate, yielding title compound (150.7 mg, 12%) 1H-NMR (CDCl3), d (ppm): 7.52 (dd, 2H), 7.19 (m, 1H), 4.21 (q, 1H), 3.78 (s, 3H), 1.64 (d, 3H).

후처리

  1. customReaction
  2. customwas partitioned between ethyl acetate (350 ml) and water 3 times
  3. washwashed with 1 M HCl, once with saturated brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customReaction
  8. extractionExtraction
  9. custompurification
  10. extractionwas performed by SPE (solid phase extraction) chromatography on silica gel using 300 ml ethyl acetate, 100 ml 1%, and 100 ml 3% formic acid in ethyl acetate

출처 및 근거

ORD 기록
ord-dae6f7238f11435fabb395d74f55e783
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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