Water → HCID 86760501, compound

HRID 1292714Notes

Reaction equation

HRID 1292714 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]([O:10][C:11]([O:13][NH:14]C(=O)OC(C)(C)C)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)C(C)C)(C)C.O>ClCCl>[C:6]([O:10][C:11]([O:13][NH:14][C:1](=[O:4])[CH:2]=[CH2:3])=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamate

Product 1

HCID 86760501HCID 86760501, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of acryloyl chloride dissolved in dry dichloromethane was cooled at 0° C. with an ice bath. A mixture of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (31) and N,N-diisopropylethylamine in dry dichloromethane was added. Water was added after 16 hours of reaction and the layers were separated. The organic solution was washed with diluted hydrochloric acid, a saturated sodium bicarbonate solution, water, and brine. The organic layer was 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). The purification gave N-(tert-butoxycarbonyl), N-(tert-butoxycarbonyloxy)acrylamide (32).

Workup

  1. additionwas added
  2. customthe layers were separated
  3. washThe organic solution was washed with diluted hydrochloric acid
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. additiona mixture of hexane and ethyl acetate (90:10)
  9. customThe purification

Sources & evidence

ORD record
ord-879c2fcbd1fe4ba5a3a3c203a5772ee3
Source dataset
uspto-grants-2007_07
Patent number
US07238339B2

Reaction notes

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