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Sodium Chloride → [(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

HRID 20339
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HRID 20339 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([O:23][CH2:24][CH3:25])=C.[I:26]N1C(=O)CCC1=O.[Cl-].[Na+].[C:36](#N)[CH3:37]>>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH:9]([O:23][CH2:24][CH2:25][I:26])[O:10][CH2:36][CH3:37])[CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 5

HCID 5234Sodium ChlorideHCID 6342AcetonitrileHCID 8023Ethyl vinyl etherHCID 120273N-IodosuccinimideHCID 10913779(R)-(+)-N-(tert-Butoxycarbonyl)-O-(tert-butyldimethylsilyl)serinol

생성물 1

HCID 86615364[(r)-2-(Tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester
수율 34%

실험 절차

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

후처리

  1. extractionExtract with ethyl acetate
  2. washwash with water and saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify
  7. wash(silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-86666333ce9343dcba6d302be914e1c2
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745438B2

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