Imidazole → HCID 87130162, compound

HRID 1640550Notes

Reaction equation

HRID 1640550 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12])([CH3:4])([CH3:3])[CH3:2].[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1>C1COCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH:9]([O:13][Si:19]([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20])[CH2:10][CH:11]=[CH2:12])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 71337422tert-Butyl (2-hydroxypent-4-en-1-yl)carbamate

Product 1

HCID 87130162HCID 87130162, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Rac-(2-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (5 g, 24.8 mmol; prepared according to Tetrahedron Lett. (2006), 47, 3295) was added dropwise to a mixture of TBDMSCl (3.7 g, 1 eq.) and imidazole (1.7 g, 1 eq.) in THF (55 mL). The mixture was stirred at rt overnight, filtered and the filtrate washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by FC (Hept/EA:1, EA) to give the title intermediate as a colourless oil (2.8 g, 36% yield).

Workup

  1. filtrationfiltered
  2. washthe filtrate washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by FC (Hept/EA:1, EA)

Sources & evidence

ORD record
ord-238c0862a9f049a19b0e98cf9cee195e
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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