Triethylamine → HCID 12810776, compound

HRID 1380496Notes

Reaction equation

HRID 1380496 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH3:9][C:10]([CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)([CH3:13])[CH:11]=[CH2:12].C(N(CC)CC)C>CN(C)C=O>[Si:5]([N:17]1[CH:14]([C:10]([CH3:13])([CH3:9])[CH:11]=[CH2:12])[CH2:15][C:16]1=[O:18])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11083962HCID 11083962, compound

Product 1

HCID 12810776HCID 12810776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylchlorosilane (7.51 g) is added in one portion to an ice-cold, stirred solution of 4-(1,1-dimethyl-prop-2-enyl)-azetidin-2-one (6.54 g) and triethylamine (5.04 g) in anhydrous dimethylformamide (100 ml). The reaction mixture is stirred at 0°-5° C. for 1 hour and then allowed to warm to room temperature. Most of the solvent is removed under vacuum to give a residue which is partitioned between diethyl ether (250 ml) and water. The ethereal phase is washed with 2.5N hydrochloric acid (50 ml), water (3×50 ml), and brine, dried with magnesium sulfate, filtered and evaporated under vacuum to provide crude product which is purified by chromatography on silica gel (20% ether in petroleum ether) to yield 2.

Workup

  1. customMost of the solvent is removed under vacuum
  2. customto give a residue which
  3. customis partitioned between diethyl ether (250 ml) and water
  4. washThe ethereal phase is washed with 2.5N hydrochloric acid (50 ml), water (3×50 ml), and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customto provide crude product which
  9. customis purified by chromatography on silica gel (20% ether in petroleum ether)
  10. customto yield 2

Sources & evidence

ORD record
ord-a58c8f4d2d114ca6bc91815d0919dcfb
Source dataset
uspto-grants-1986_04
Patent number
US04582643

Reaction notes

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