Hydrochloric Acid → tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate

HRID 1174262ノート

反応式

HRID 1174262 の反応式
[Br:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][C:7]2(C(OCC)=O)[CH2:11][C@@H:10]([C@@H:12]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:9][C:8]2=[O:28])=[CH:4][CH:3]=1.Cl>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:8](=[O:28])[O:9][C@H:10]([C@@H:12]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11]2)=[CH:34][CH:35]=1

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 67406735ethyl (5S)-3-(4-bromobenzyl)-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-2-oxotetrahydro-3-furancarboxylate

生成物 1

HCID 86598818tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate収率 94.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

A solution of the product from Example 92A (22.4 g) in ethanol (120 mL) was treated with LiOH monohydrate (8.0 g, 190.7 mmol) solution in water (30 mL) and the mixture was stirred at 25° C. for 16 hours. The mixture was cooled to 0° C., adjusted to pH 5 by addition of 4N HCl and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate in toluene (400 mL) was then heated at reflux for 18 hours, cooled and concentrated to give the title compound (18.4 g), which was used without further purification.

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. custompartitioned between dichloromethane and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationA solution of the concentrate in toluene (400 mL)
  8. temperaturewas then heated
  9. temperatureat reflux for 18 hours
  10. temperaturecooled
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-bca720b1212c459aba21c7687ab1d6f9
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

反応ノート

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