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Sodium hydride → HCID 11371084, 화합물

HRID 1368759
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HRID 1368759 반응식
[Si:1]([O:8][C@@H:9]([C@@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]Cl)[CH2:10][Cl:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[C:19]([O:18][C:16]([N:15]1[CH2:13][C@@H:12]1[C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][Cl:11])=[O:17])([CH3:22])([CH3:21])[CH3:20]
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참가 물질

5

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HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 111995852S-t-Butyldimethylsilyloxy-3R-(t-Boc)-amino-1,4-dichlorobutane

생성물 1

HCID 11371084HCID 11371084, 화합물수율 100.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a magnetically stirred solution of 2(S)-t-butyldimetylsilyloxy-3(R)-(t-butyloxycarbonyl)amino-1,4-dichlorobutane (375.4 mg, 1.008 mmol) in THF (10 mL) was added NaH slowly at 0° C. under N2. After 5 h, the reaction mixture was slowly added to sat aq ammonium chloride solution (40 mL) and ice (20 g). The resulting solution was extracted with EtOAc (60 mL 4). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered, concentrated and column chromatographed (10% EtOAc in n-Hex) to provide N-t-butyloxycarbonyl-2(R)-(1(S)-t-butyldimetylsilyloxy-2-chloroethyl)aziridine (339.5 mg) as a colorless oil.

후처리

  1. additionthe reaction mixture was slowly added
  2. extractionThe resulting solution was extracted with EtOAc (60 mL 4)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customcolumn chromatographed (10% EtOAc in n-Hex)

출처 및 근거

ORD 기록
ord-4bede00db9f54e26b555ac1f881ace4b
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06573388B1

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