Hydrochloric Acid → Tert-butyl 1,3-thiazole-4-carboxylate

HRID 539652

반응식

HRID 539652 반응식
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=[O:7])[N:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:21](O)([CH3:24])([CH3:23])[CH3:22].C1CCN2C(=NCCC2)CC1.Cl>CN(C=O)C.O>[S:1]1[CH:5]=[C:4]([C:6]([O:8][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:7])[N:3]=[CH:2]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3042714-Thiazolecarboxylic acid

생성물 1

HCID 16744294Tert-butyl 1,3-thiazole-4-carboxylate수율 47%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of thiazole-4-carboxylic acid 7.1 (1 g, 7.2 mmol) and carbonyldiimidazole (6.3 g, 38.7 mmol) in commercial dry DMF (50 mL) under N2 was stirred at 50° C. for 20 min. Tert-butanol (8.6 g, 116.0 mmol) and DBU (5.8 mL, 38.7 mmol) were then successively added at once and the reaction was warmed at 60° C. for 48 h. The RM was then allowed to cool down to RT and the pH was adjusted to 4 with a solution of HCl (2M, ˜80 mL). The mixture was diluted with water (250 mL) and extracted with Et2O (3×100 mL). The combined org. layers were washed with brine (250 mL), dried over MgSO4, concentrated and purified on silica gel using DCM to afford title product as yellowish oil (47%). Yield: 3.37 g (47%). LCMS: P=98%, rt=3.65 nm, m/z=186.

후처리

  1. temperatureto cool down to RT
  2. extractionextracted with Et2O (3×100 mL)
  3. washlayers were washed with brine (250 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel

출처 및 근거

ORD 기록
ord-beb5a80539924462b21bb4ef310f3bf3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871761B2

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