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

HRID 495060Notes

Reaction equation

HRID 495060 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-562440d0eacc40aa89987591eca386e7
Source dataset
uspto-grants-2009_05
Patent number
US07538223B2

Reaction notes

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