Isopropenyl chloroformate → HCID 90445230, compound

HRID 626526Notes

Reaction equation

HRID 626526 reaction equation
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([NH2:6])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:20]([O:22][C:23]([CH3:25])=[CH2:24])=[O:21]>C1COCC1>[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([NH:6][C:20](=[O:21])[O:22][C:23]([CH3:25])=[CH2:24])=[O:5]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 125785442-Methoxy-2-methylpropanamide

Product 1

HCID 90445230HCID 90445230, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. solution of 2-methoxy-2-methylpropanamide (0.25 g, 2.134 mmol) in THF (6 mL) was treated drop-wise with lithium bis(trimethylsilyl)amide (1M in THF, 2.77 mL, 2.77 mmol) stirred for 0.5 h. A solution of isopropenyl chloroformate (0.257 mL, 2.347 mmol) in THF (1 mL) was added drop-wise and the mixture was stirred at −78° C. for 1 h. The mixture was warmed to RT, stirred for 1 h, quenched with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford prop-1-en-2-yl (2-methoxy-2-methylpropanoyl)carbamate (440 mg, 102%). MS (ESI) m/z: 202.1 (M+H+).

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. stirringstirred for 1 h
  3. customquenched with satd
  4. extractionNaHCO3, extracted with EtOAc (3×)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1a7f754b2f2d47fb889f30b70ee090e8
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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