Imidazole → Di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate

HRID 495060노트

반응식

HRID 495060 반응식
[OH:1][CH:2]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].CCOCC>CN(C=O)C.[Cl-].[Na+].O>[Si:26]([O:1][CH:2]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 375632tert-butyl N-{3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}carbamate

생성물 1

HCID 57683620Di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate수율 86.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To 29.0 g (0.1 mol) of di-tert-butyl 2-hydroxypropane-1,3-diyldicarbamate and 17.0 g (0.25 mol) of imidazole in 200 ml DMF at 0° C., was added 18.09 g (0.12 mol) of t-butyldimethylsilylchloride (TBDSMCl) in portions. The reaction was warmed up to RT and stirred for 2 hours. To this mixture was added 400 ml ether and 400 ml brine. The layers were separated and the aqueous layer was extracted with 400 ml ether. The combined organic layer was dried and concentrated to give 35 g of di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diyldicarbamate (86% yield).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with 400 ml ether
  3. customThe combined organic layer was dried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-562440d0eacc40aa89987591eca386e7
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538223B2

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