Water → Methyl 3-(3,6-dihydro-2H-pyran-4-yl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate

HRID 1662432ノート

反応式

HRID 1662432 の反応式
C1([C@H](C2C=CC=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20](C4C=C(OC)C=CC=4F)=[C:19]([C@@H:32]4[CH2:36][CH2:35]C[C:33]4([CH3:38])C)[CH:18]=3)C=2)CC(O)=O)CC1.C[O:40][C:41]1[CH:42]=[CH:43][CH:44]=[C:45]([O:66]C)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-:68]P([O-])([O-])=O.[K+].[K+].[K+].[OH2:76]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:76]1[CH2:38][CH:33]=[C:32]([C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=2[O:66][CH:45]2[CH2:44][CH2:43][CH2:42][CH2:41][O:40]2)[C:16]([O:15][CH3:11])=[O:68])[CH2:36][CH2:35]1

参加物

7

反応物 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57706097(3r)-3-Cyclopropyl-3-(3-(((2-((1r)-2,2-dimethylcyclopentyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acid

生成物 1

HCID 57706658Methyl 3-(3,6-dihydro-2H-pyran-4-yl)-4-(tetrahydro-2H-pyran-2-yloxy)benzoate収率 52%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A stirred mixture of 66.6 F (1.40 g, 4.45 mmol), ground S-Phos (0.38 g, 0.920 mmol), palladium acetate (0.11 g, 0.475 mmol), 66.46B (1.40 g, 6.65 mmol), and potassium phosphate tribasic (2.48 g, 11.7 mmol) in DMF (10.0 mL) and water (0.5 mL) was purged three times with argon. The mixture was heated to 75° C. and monitored with LC-MS. After 21 hours, the reaction was cooled to room temperature and then diluted with water and extracted three times with EtOAc. The organic layers were combined and washed twice with brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was purified on silica gel using 0-20% EtOAc in hexanes to afford 66.46C as a colorless oil (0.73 g, 52% yield). MS ESI (pos.) m/e: 340.9 (M+Na)+.

後処理

  1. customwas purged three times with argon
  2. temperaturethe reaction was cooled to room temperature
  3. additiondiluted with water
  4. extractionextracted three times with EtOAc
  5. washwashed twice with brine
  6. dry with materialAfter drying over anhydrous sodium sulfate and filtration
  7. customthe organic solvent was removed under reduced pressure
  8. customThe residue was purified on silica gel using 0-20% EtOAc in hexanes

出典と根拠

ORDレコード
ord-4236fb732c7c476d92fac32f2a9d761e
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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