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

HRID 31362

반응식

HRID 31362 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:4][CH:3]=1.[CH2:25]=[O:26].[OH-].[Na+]>C1COCC1>[OH:1][C:2]1[C:10]([CH2:25][OH:26])=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][C@@H:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 135487328Benzyl (S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of benzyl [(1S)-2-(6-hydroxy-1H-indazol-1-yl)-1-methylethyl]carbamate (30.83 g, 0.0949 mol) in THF (400 ml) was treated with aqueous concentrated formaldehyde (37%, 12 M. 0.285 mol, 24 mL) and cooled in an ice bath. To the mixture was slowly added aqueous 1 N sodium hydroxide (0.02 mol, 20 mL) and the reaction was allowed to warm to room temperature while stirring overnight. The reaction was quenched with aqueous saturated sodium bicarbonate (250 mL) and then neutralized to pH 7 with aqueous 2 N hydrochloric acid. The mixture was extracted with ethyl acetate (200 mL×3), the combined organic layers were dried over magnesium sulfate and filtered and evaporated to give crude tan solid, 28.38 g, which was a mixture of desired product and dimerized byproduct by LC/MS 356 m/z and 663 m/z. This residue was purified by chromatography (silica gel, hexane/ethyl acetate 1:1) to give the title compound, (18.44 g, 56%) as a yellow foamy solid, which was not pure by LS/MS 354 m/z with minor 663 m/z.

후처리

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with aqueous saturated sodium bicarbonate (250 mL)
  3. extractionThe mixture was extracted with ethyl acetate (200 mL×3)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude tan solid, 28.38 g, which

출처 및 근거

ORD 기록
ord-bfb01c5aa2d84f0398523e4456f98058
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425572B2

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