Trimethylacetamide → HCID 90403542, compound

HRID 1049377Notes

Reaction equation

HRID 1049377 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH2:5])=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:19]([O:21][C:22]([CH3:24])=[CH2:23])=[O:20]>C1COCC1>[C:3]([NH:5][C:19](=[O:20])[O:21][C:22]([CH3:24])=[CH2:23])(=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1]

Participants

5

Reactant 3

HCID 12957TrimethylacetamideHCID 93846Isopropenyl chloroformateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 90403542HCID 90403542, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. solution of 2,2,2-trimethylacetamide (1 g, 9.89 mmol) in THF (20 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1.0N in THF, 11.86 mL, 11.86 mmol), stirred for 30 min, treated drop-wise with a solution of isopropenyl chloroformate (1.43 g, 11.86 mmol) in THF (5 mL), warmed to RT and stirred for 1 h. The mixture was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with satd. NH4Cl, then brine, dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl pivaloylcarbamate (1.94 g, 106%) which was used without further purification.

Workup

  1. stirringstirred for 1 h
  2. additionThe mixture was treated with satd
  3. extractionNaHCO3, extracted with EtOAc (2×)
  4. washthe combined organics were washed with satd
  5. dry with materialNH4Cl, then brine, dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-263ff9206f034c7191fc34918ffbf972
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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