Benzyl {(1S)-2-[6-hydroxy-7-(hydroxymethyl)-1H-indazol-1-yl]-1-methylethyl}carbamate → Benzyl [(1S)-2-(7-formyl-6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate

HRID 31363

반응식

HRID 31363 반응식
[OH:1][C:2]1[C:10]([CH2:11][OH:12])=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:15])=[CH:4][CH:3]=1>C(OCC)(=O)C>[CH:11]([C:10]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:9]=1[N:8]([CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:15])[N:7]=[CH:6]2)=[O:12]

참가 물질

3

반응물 1

HCID 135427951Benzyl {(1S)-2-[6-hydroxy-7-(hydroxymethyl)-1H-indazol-1-yl]-1-methylethyl}carbamate

생성물 1

HCID 136385114Benzyl [(1S)-2-(7-formyl-6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate수율 35%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
47.5 °C

실험 절차

A solution of the compound from Step A (18.44 g, 0.0519 mol) in ethyl acetate (180 mL) was treated with mangenese dioxide (fine powder, 18 g) and stirred at 45-50° C. for two days. Then the reaction stood at room temperature one day. The mixture was filtered and the black solids were rinsed with ethyl acetate. The organic filtrate was evaporated to a tan foam. The residue was purified by chromatography (silica gel, hexane/ethyl acetate 1:1) to give the title compound, (6.32 g, 35%) as a pale yellow fluffy solid, which was pure by LS/MS 354 m/z.

후처리

  1. waitThen the reaction stood at room temperature one day
  2. filtrationThe mixture was filtered
  3. washthe black solids were rinsed with ethyl acetate
  4. customThe organic filtrate was evaporated to a tan foam
  5. customThe residue was purified by chromatography (silica gel, hexane/ethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-c9f6e9f88df6466cbf88d76d2fd5b741
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425572B2

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