Cerous carbonate → HCID 123262148, 화합물

HRID 1498838

반응식

HRID 1498838 반응식
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

참가 물질

5

반응물 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

생성물 1

HCID 123262148HCID 123262148, 화합물수율 52.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e943a5067c014b4ba4e657bbf87c2da6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200002B2

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