Methyl chloroformate → HCID 22096111, compound

HRID 2230011Notes

Reaction equation

HRID 2230011 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][NH:10][C:11](=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].Cl[C:22]([O:24][CH3:25])=[O:23]>O1CCCC1>[CH3:8][O:9][N:10]([C:22]([O:24][CH3:25])=[O:23])[C:11](=[O:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 18671325HCID 18671325, compound

Product 1

HCID 22096111HCID 22096111, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round-bottom flask equipped with a magnetic stir bar, argon inlet and pressure equalizing addition funnel is charged with tetrahydrofuran (14.0 mL), triethylamine (2.13 g, 1.5 eq) and N-methoxynonanamide (1.96 g, 1 eq). The reaction is cooled in an ice bath and methyl chloroformate (1.88 g, 1.4 eq) is added dropwise. The reaction is allowed to warm to room temperature overnight. The tetrahydrofuran is removed under vacuum and the residue is diluted with methylene chloride (25 mL). The reaction is washed with 0.1 M hydrochloric acid solution (1×20 mL), saturated aqueous sodium bicarbonate (3×20 mL) and brine (1×20 mL). The organic layer is dried over sodium sulfate, filtered and concentrated under vacuum.

Workup

  1. customA 100 mL round-bottom flask equipped with a magnetic stir bar, argon inlet
  2. additionaddition funnel
  3. temperatureThe reaction is cooled in an ice bath
  4. customThe tetrahydrofuran is removed under vacuum
  5. additionthe residue is diluted with methylene chloride (25 mL)
  6. washThe reaction is washed with 0.1 M hydrochloric acid solution (1×20 mL), saturated aqueous sodium bicarbonate (3×20 mL) and brine (1×20 mL)
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8a0a9ae68a8d45a4947da73b2d90695e
Source dataset
uspto-grants-2002_07
Patent number
US06423676B1

Reaction notes

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