Ethanol → HCID 22242839, 화합물

HRID 891590노트

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HRID 891590 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 22242839HCID 22242839, 화합물수율 18%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-041316a3a1a14f9986a0268e37d630b0
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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