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

HRID 20505ノート

反応式

HRID 20505 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-551d67b9c8754d62bbc83a72a7e5e48c
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

読み込み中…