Cerous carbonate → HCID 123262148、化合物

HRID 1498838

反応式

HRID 1498838 の反応式
CS(O[CH2:6][C@H:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[CH3:20][C:21]1([CH3:33])[C:25]([CH3:27])([CH3:26])[O:24][B:23]([C:28]2[CH:29]=[N:30][NH:31][CH:32]=2)[O:22]1.C(=O)([O-])[O-].[Ce+3].C(=O)([O-])[O-].C(=O)([O-])[O-].[Ce+3]>C(#N)C>[CH3:20][C:21]1([CH3:33])[C:25]([CH3:26])([CH3:27])[O:24][B:23]([C:28]2[CH:32]=[N:31][N:30]([CH2:6][C@H:7]3[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8]3)[CH:29]=2)[O:22]1

参加物

5

反応物 3

HCID 160516Cerous carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86673567(S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

生成物 1

HCID 123262148HCID 123262148、化合物収率 52.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To a mixture of (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate (430 mg, 1.46 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (283 mg, 1.46 mmol) in 50 mL of acetonitrile was added cerium carbonate (1.43 g, 4.37 mmol), and the mixture was stirred at 60° C. for 3 h. TLC and LCMS showed the reaction was completed. After the solvents were removed under reduced pressure, the residue was diluted with 50 mL of ethyl acetate, and washed with water (50 mL×3) and brine. The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate=5:1) to get the title product (300 mg, 52%) as colorless oil. MS (ES+) C19H32BN3O5 requires: 393. found: 394 [M+H]+.

後処理

  1. customAfter the solvents were removed under reduced pressure
  2. additionthe residue was diluted with 50 mL of ethyl acetate
  3. washwashed with water (50 mL×3) and brine
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (petroleum ether:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-e943a5067c014b4ba4e657bbf87c2da6
出典データセット
uspto-grants-2015_12
特許番号
US09200002B2

関連ノート

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