Triethylamine → HCID 22991103, compound

HRID 1168115Notes

Reaction equation

HRID 1168115 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][C:11]([O:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:17]([O:16][C:15]([N:14]([O:13][C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[C:1](=[O:4])[CH:2]=[CH2:3])=[O:21])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamate

Product 1

HCID 22991103HCID 22991103, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of acryloyl chloride (700 μL; 779.8 mg; 8.6 mmole) dissolved in dry dichloromethane (20 mL) was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) (2.0038 g; 8.6 mmole) and triethylamine (1.32 mL; 958.3 mg; 9.5 mmole) in dry dichloromethane (20 mL) was slowly added over a period of 1 hour to the cooled solution. The ice bath was removed after 4 hours and the reaction mixture was left stirring overnight while its temperature warmed up gradually to room temperature. Water (100 mL) was added to the reaction and the layers were separated. The organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL). The organic layer was then dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure. The residue was purified by flash chromatography using a mixture of hexane and ethyl acetate (90:10) to elute the product. The purification gave 690 mg (28%) of N-(tert-butoxycarbonyl),N-(tert-butoxycarbonyloxy)acrylamide (32) as a colorless oil.

Workup

  1. additionwas slowly added over a period of 1 hour to the cooled solution
  2. customThe ice bath was removed after 4 hours
  3. waitthe reaction mixture was left
  4. temperaturewarmed up gradually to room temperature
  5. additionWater (100 mL) was added to the reaction
  6. customthe layers were separated
  7. washThe organic solution was washed with a 10% ammonium chloride solution (3×80 mL), water (2×100 mL), and finally brine (1×100 mL)
  8. dry with materialThe organic layer was then dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure
  11. customThe residue was purified by flash chromatography
  12. additiona mixture of hexane and ethyl acetate (90:10)
  13. washto elute the product
  14. customThe purification

Sources & evidence

ORD record
ord-5f6f6d2be631449dae8d40a48041711c
Source dataset
uspto-grants-2003_09
Patent number
US06623721B2

Reaction notes

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