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

HRID 495060ノート

反応式

HRID 495060 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-562440d0eacc40aa89987591eca386e7
出典データセット
uspto-grants-2009_05
特許番号
US07538223B2

反応ノート

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