Imidazole → N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide

HRID 76239Notes

Reaction equation

HRID 76239 reaction equation
[C:1]([NH:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O.CCOCC>CN(C=O)C>[C:9]([NH:8][CH2:7][CH:6]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 332254HCID 332254, compoundHCID 21584184Diethylether water

Product 1

HCID 86698889N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-(3-acetylamino-2-hydroxypropyl)acetamide (synthesized as described in J. Org. Chem., 2000, 65(4), 1200, which is incorporated herein by reference in its entirety) (741 mg, 4.25 mmol) and 1H-imidazole (579 mg, 8.51 mmol) in dry DMF (17 mL), a solution of tert-butylchlorodimethylsilane (962 mg, 6.38 mmol) in dry DMF (8 mL) was added dropwise, and the reaction was stirred at r.t. overnight. The reaction was portioned between H2O/Et2O, the phases were separated and the aqueous layer was washed twice with Et2O and three times with EtOAc. All the organics were combined, dried over Na2SO4, filtered and concentrated, affording N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide (1140 mg, 3.95 mmol, 93% yield) as off-white solid.

Workup

  1. customthe phases were separated
  2. washthe aqueous layer was washed twice with Et2O and three times with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-517a872a26be4324b062ae8078ef9fc6
Source dataset
uspto-grants-2014_09
Patent number
US08835494B2

Reaction notes

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