Imidazole → HCID 59750865, compound

HRID 748797Notes

Reaction equation

HRID 748797 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].N1C=CN=C1.[C:20]([Si:24](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])([CH3:22])[CH3:21].CCCCCC>ClCCl.CN(C)C=O.C(OCC)(=O)C>[Si:24]([O:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][OH:14])[C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8058HexaneHCID 94078tert-ButyldiphenylchlorosilaneHCID 4360601N-Boc-diethanolamine

Product 1

HCID 59750865HCID 59750865, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

In a dichloromethane/N,N-dimethylformamide (70 ml/70 ml) mixture were dissolved t-butyl N,N-bis(2-hydroxyethyl)carbamate (9.00 g, 43.8 mmol) and imidazole (2.60 g, 38.2 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (8.1 ml, 31 mmol) at room temperature. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. The resulting mixture was washed with water and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (7.41 g, 16.7 mmol, 54%) was obtained as a colorless oil.

Workup

  1. additionAfter completion of the dropwise addition
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture under reduced pressure
  4. additionwas added with diethyl ether
  5. washThe resulting mixture was washed with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue thus obtained

Sources & evidence

ORD record
ord-5c5ca53811f642fea10bfd8baf26d2df
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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