Ethanol → HCID 22242839、化合物

HRID 891590ノート

反応式

HRID 891590 の反応式
[C:1]([N:4]1[CH2:7][CH:6]([OH:8])[CH2:5]1)(=[O:3])[NH2:2].[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1.C(O)C>CN(C)C=O>[Si:9]([O:8][CH:6]1[CH2:7][N:4]([C:1](=[O:3])[NH2:2])[CH2:5]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 702EthanolHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 222430703-Hydroxyazetidine-1-carboxamide

生成物 1

HCID 22242839HCID 22242839、化合物収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-carbamoyl-3-hydroxyazetidine (obtained as described in Reference Example 21(1)) in dimethylformamide (100 ml) were added t-butyldiphenylsilyl chloride (18.0 ml, 66.9 mmol) and imidazole (4.55 g, 66.9 mmol) in an ice bath. After stirring the mixture in an ice bath for 10 minutes, the resulting mixture was stirred at room temperature overnight. After checking the completion of the reaction, ethanol (1 ml) was added to the reaction mixture in an ice bath and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-carbamoylazetidine (1.45 g, total yield 18%) as a white solid.

後処理

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. additionwas added to the reaction mixture in an ice bath
  3. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  4. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution
  5. washThe organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-041316a3a1a14f9986a0268e37d630b0
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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