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Water → tert-butyl (6R,7R)-6-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022689
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HRID 1022689 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[CH2:23][NH:24][CH2:25][CH2:26][OH:27])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:35]([Si:39](Cl)([CH3:41])[CH3:40])([CH3:38])([CH3:37])[CH3:36].O>C1COCC1>[Si:39]([O:27][CH2:26][CH2:25][NH:24][CH2:23][C@H:10]1[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:41])[CH3:40]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471Triethylamine2회HCID 28928tert-Butyldimethylsilyl chloride2회HCID 66975933tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-hydroxyethyl)amino]methyl}-1,4-oxazepane-4-carboxylate

생성물 1

HCID 66974980tert-butyl (6R,7R)-6-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate
수율 93.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a solution (13.2 mL) of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-hydroxyethyl)amino]methyl}-1,4-oxazepane-4-carboxylate (1.65 g) and triethylamine (0.605 mL) in THF was added, under ice-cooling, tert-butylchlorodimethylsilane (654 mg), and the mixture was stirred at room temperature overnight. Then, tert-butylchlorodimethylsilane (654 mg) and triethylamine (0.605 mL) were added, and the mixture was stirred at 50° C. for 1 hr. Distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.96 g).

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-0e3eeccc88b240319b19f193c3cb2bef
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722662B2

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