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Diisopropylethylamine → n-Trimethylsilylethoxycarbonyl-1,2-diaminoethanehydrochloride

HRID 353689
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HRID 353689 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])(C)(C)[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:21][Si:22](CCOC([Cl:30])=O)([CH3:24])[CH3:23]>C1COCC1.ClCCl>[ClH:30].[CH3:21][Si:22]([CH2:2][CH2:1][O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:24])[CH3:23]
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 109101682-(Trimethylsilyl)ethyl chloroformate

생성물 1

HCID 23511190n-Trimethylsilylethoxycarbonyl-1,2-diaminoethanehydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran
용매

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온도
0 °C

실험 절차

N-(t-Butyloxycarbonyl)-1,2-diaminoethane (8.0 g, 50 mmol) is dissolved in THF (200 mL), diisopropylethylamine (6.5 g, 50 mmol) is added and the solution cooled to 0° C. To this cold solution is added dropwise trimethylsilylethoxycarbonylchloride (9.0 g, 50 mmol) over 10 minutes. After stirring an additional 30 minutes the reaction is filtered and the filtrate is evaporated to an oil. This oil is dissolved in 100 mL of diethyl ether and washed with dilute HCl solution (3×25 mL), dried, filtered and evaporated to give an oil. The oil is dissolved in 100 mL of dichloromethane and dry HCl gas is bubbled through the solution for 30 minutes and the reaction stirred for 1 hour. The reaction is diluted with 200 mL of cold diethyl ether and allowed to stand at −5° C. for 12 hours. The colorless solid formed is collected and stored protected from moisture.

후처리

  1. filtrationis filtered
  2. customthe filtrate is evaporated to an oil
  3. dissolutionThis oil is dissolved in 100 mL of diethyl ether
  4. washwashed with dilute HCl solution (3×25 mL)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. customdry HCl gas is bubbled through the solution for 30 minutes
  10. stirringthe reaction stirred for 1 hour
  11. additionThe reaction is diluted with 200 mL of cold diethyl ether
  12. waitto stand at −5° C. for 12 hours
  13. customThe colorless solid formed
  14. customis collected

출처 및 근거

ORD 기록
ord-53d2033c6d474acebaff76f30fc75f7d
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06756199B1

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