Potassium Carbonate → Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

HRID 20505노트

반응식

HRID 20505 반응식
[Si]([O:8][CH2:9][C@H:10]([CH3:23])[O:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])(C(C)(C)C)(C)C.[F:24][C:25]1[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=1F)[C:28]([N:30]1[CH2:33][CH2:32][CH2:31]1)=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:30]1([C:28]([C:27]2[CH:34]=[CH:35][C:36]([O:22][C:20]3[CH:19]=[C:14]([CH:13]=[C:12]([O:11][C@@H:10]([CH3:23])[CH2:9][OH:8])[CH:21]=3)[C:15]([O:17][CH3:18])=[O:16])=[C:25]([F:24])[CH:26]=2)=[O:29])[CH2:33][CH2:32][CH2:31]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 593468591-(3,4-Difluorobenzoyl)azetidineHCID 59346877methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate

생성물 1

HCID 59346922Methyl 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
160 °C

실험 절차

To a portion of methyl 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-hydroxybenzoate (102 mg, 0.3 mmol) and 1-(3,4-difluorobenzoyl)azetidine (71 mg, 0.36 mmol) in DMF (2.0 mL) was added potassium carbonate (207 mg, 1.5 mmol) and the stirred mixture heated at 160° C. in a ‘Smith Creator Microwave’ for 120 minutes. The mixture was allowed to reach ambient temperature and pressure then partitioned between ethyl acetate (2×25 mL) and water (25 mL). The organic layer was separated, washed with brine, dried (MgSO4), and evaporated in vacuo to give the crude product which was used without further purification (100 mg).

후처리

  1. customto reach ambient temperature
  2. custompressure then partitioned between ethyl acetate (2×25 mL) and water (25 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-551d67b9c8754d62bbc83a72a7e5e48c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

반응 노트

불러오는 중…