Water → (R)-[1-(2-cyano-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester

HRID 1645147ノート

反応式

HRID 1645147 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:20][CH2:19][CH2:18][C:17]2[N:16]([CH2:21][CH2:22]OS(C)(=O)=O)[N:15]=[CH:14][C:13]1=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:28]#[N:29].[Na+].O>CS(C)=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@@H:12]1[CH2:20][CH2:19][CH2:18][C:17]2[N:16]([CH2:21][CH2:22][C:28]#[N:29])[N:15]=[CH:14][C:13]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 59152906methanesulfonic acid 2-((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydroindazol-1-yl)-ethyl ester

生成物 1

HCID 59152880(R)-[1-(2-cyano-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester収率 85.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

To a solution of methanesulfonic acid 2-((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydroindazol-1-yl)-ethyl ester (850 mg, 2.16 mmol) in dimethyl sulfoxide (20 mL) was added sodium cyanide (540 mg, 10.8 mmol). The mixture was stirred at 55° C. for 4 hours. After cooling, to the mixture was added water, and the aqueous layer was extracted with ethyl acetate (20 mL×4). The combined organic layers were dried over sodium sulfate, filtered and then concentrated in vacuo. The residue was purified by flash column chromatography (10% methanol in dichloromethane) to afford (R)-[1-(2-cyano-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester (600 mg, 85%) as a white solid. MS calcd. for C18H20N4O2 324, obsd. (ESI+) [(M+H)+] 325.

後処理

  1. temperatureAfter cooling, to the mixture
  2. extractionthe aqueous layer was extracted with ethyl acetate (20 mL×4)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-8cb25dc497d544479208995d38d8c8df
出典データセット
uspto-grants-2012_02
特許番号
US08124641B2

反応ノート

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