Imidazole → [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester

HRID 891631노트

반응식

HRID 891631 반응식
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@H:11]([CH2:14][OH:15])[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:17](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CN=C1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@H:11]([CH2:14][O:15][Si:17]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 10263004benzyl N-((2S)-1-hydroxybutan-2-yl)carbamate

생성물 1

HCID 60109785[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester수율 107.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Subsequently, to a solution of [(1S)-1-(hydroxymethyl)propyl]carbamic acid benzyl ester (4.27 g, 19.1 mmol) in dimethylformamide (128 ml) were added t-butyldiphenylsilyl chloride (5.97 ml, 22.9 mmol) and imidazole (1.56 g, 22.9 mmol) in an ice bath. The mixture was stirred at room temperature overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (6:1→4:1) as the eluant to afford [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (9.48 g, yield 100%) as a white solid.

후처리

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  3. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-8d99b719df7a411a8fc98cb0fdfab74f
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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