Thiazole → HCID 178451152, 화합물

HRID 2272670노트

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HRID 2272670 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[C:11]([C@@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:16][CH2:15]1)(=[O:13])[CH3:12]>C1COCC1.O>[OH:13][C:11]([C@@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH2:16][CH2:15]1)([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH3:12]

참가 물질

6

반응물 3

HCID 9256ThiazoleHCID 178418339ButyllithiumHCID 178451154HCID 178451154, 화합물

생성물 1

HCID 178451152HCID 178451152, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

A solution of thiazole (800 mg, 9.40 mmol) in THF (94 mL) was cooled to −78° C. nBuLi (2.5 M in THF, 3759 μl, 9.40 mmol) was added and the solution was stirred for 30 minutes at −78° C. Butyl cis-4-acetylcyclohexanecarboxylate (2552 mg, 11.28 mmol) in THF (5 mL) was added in one portion and the solution was stirred for one hour at −78° C. The reaction was diluted with water and then warmed to room temperature. The mixture was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5-30% ethyl acetate/hexanes) to afford cis-butyl 4-[1-hydroxy-1-(1,3-thiazol-2-yl)ethyl]cyclohexanecarboxylate. MS ESI calc'd. for C16H25NO3S [M+H+] 312. found 312.

후처리

  1. additionwas added
  2. stirringthe solution was stirred for one hour at −78° C
  3. temperaturewarmed to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (5-30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-26c895a52e3d4aae92820065292b31a9
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120785B2

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