Lithium Hydroxide → (2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

HRID 2252713노트

반응식

HRID 2252713 반응식
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@H:32]([CH2:34][O:35]C(=O)C3C=CC=CC=3)[C@@H:22]([O:23]C(=O)C3C=CC=CC=3)[C@@:12]2([CH3:44])[O:13]C(=O)C2C=CC=CC=2)=[C:4]([Cl:45])[N:3]=1.[Li+].[OH-]>C1COCC1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:33][C@H:32]([CH2:34][OH:35])[C@@H:22]([OH:23])[C@@:12]2([CH3:44])[OH:13])=[C:4]([Cl:45])[N:3]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 58730438(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-((benzoyloxy)methyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

생성물 1

HCID 11313089(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To the crude compound from Step A (2.54 g) in THF (18 mL) was added aqueous 2N LiOH (6 mL). The resulting mixture was stirred at room temperature for 3 h, the THF evaporated in vacuo and the resulting aqueous phase neutralized by addition of aqueous 2N hydrochloric acid. The mixture was adsorbed onto silica gel by evaporation in vacuo and purified on silica gel using methanol/dichloromethane (1:4) as the eluent. Fractions containing the product were combined and evaporated in vacuo to give the desired product as a colorless powder.

후처리

  1. customthe THF evaporated in vacuo
  2. additionthe resulting aqueous phase neutralized by addition of aqueous 2N hydrochloric acid
  3. customThe mixture was adsorbed onto silica gel by evaporation in vacuo
  4. custompurified on silica gel
  5. additionFractions containing the product
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-c1615b7b837c480188d0f5013f62e16c
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323453B2

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