Ethyl bromoacetate → [1-((S)-2-Benzyloxycarbonylamino-propyl)-7-bromo-1H-indazol-6-yloxy]-acetic acid ethyl ester

HRID 31365

反応式

HRID 31365 の反応式
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C@@H:11]([CH3:24])[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([OH:23])[C:20]=2[Br:22])[CH:15]=[N:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CC(C)=O>[CH2:37]([O:36][C:34](=[O:35])[CH2:33][O:23][C:19]1[C:20]([Br:22])=[C:21]2[C:16]([CH:15]=[N:14][N:13]2[CH2:12][C@@H:11]([NH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:25])[CH3:24])=[CH:17][CH:18]=1)[CH3:38]

参加物

5

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 136207273Benzyl (S)-2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

生成物 1

HCID 69253335[1-((S)-2-Benzyloxycarbonylamino-propyl)-7-bromo-1H-indazol-6-yloxy]-acetic acid ethyl ester収率 84.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of the compound from Step A (0.90 g, 2.23 mmol), potassium carbonate (0.40 g, 2.90 mmol) in acetone (80 mL) was added ethyl bromoacetate (0.484 g, 0.32 mL, 2.90 mmol) with stirring. The mixture was heated at reflux temperature for 3 h and evaporated to dryness. The residue was mixed with water (100 mL) and extracted with EtOAc (3×60 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. Chromatography on silica eluting with a gradient of 10% to 30% EtOAc/hexane gave a solid (0.92 g, 84%): mp 89-90° C.; LCMS (+APCI) 490, 492 (M+H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. customevaporated to dryness
  4. additionThe residue was mixed with water (100 mL)
  5. extractionextracted with EtOAc (3×60 mL)
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-25122af1ac5b4d528180be0844a2e284
出典データセット
uspto-grants-2008_09
特許番号
US07425572B2

関連ノート

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