Triethylamine → HCID 11716656, compound

HRID 747472Notes

Reaction equation

HRID 747472 reaction equation
[Si:1]([CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH:13]([OH:16])[CH2:14][NH2:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:24](Cl)(=[O:28])[C:25]([CH3:27])=[CH2:26]>C(Cl)Cl>[OH:16][CH:13]([CH2:12][O:11][CH2:10][CH2:9][CH2:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH2:14][NH:15][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chloride2×HCID 21097415HCID 21097415, compound

Product 1

HCID 11716656HCID 11716656, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(3-(t-Butyldimethylsilyl)propyloxy)-2-hydroxypropylamine (19.0 g, 0.077 mol), triethylamine (7.8 g, 10.8 mL, 0.08 mol), and methylene chloride (57 mL) were mixed in a 250 mL one-neck flask which was placed in an ice bath. To the above mixture, methacryloyl chloride (8.3 g, 7.73 mL, 077 mol) was added dropwise through an additional funnel at 0° C. After the completion of the addition of methacryloyl chloride, the whole mixture was allowed to warm up to room temperature and stirred at ambient temperature for two days. The reaction suspension was diluted with 100 mL of methylene chloride and washed with deionized water, 0.5 N sodium hydroxide aqueous solution, 5% sodium chloride solution in water twice and saturated sodium chloride aqueous solution in sequence. The organic phase was dried over sodium sulfate. After the removal of sodium sulfate by filtration, the solvent was evaporated by using a rotary evaporator under vacuum. N-[2-Hydroxy-3-(3-(t-butyldimethylsilyl)propyloxy)propyl]-2-methyl acrylamide was obtained as a white solid after purification by silica gel column chromatography.

Workup

  1. customwas placed in an ice bath
  2. washwashed with deionized water, 0.5 N sodium hydroxide aqueous solution, 5% sodium chloride solution in water twice
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customAfter the removal of sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was evaporated
  7. customa rotary evaporator under vacuum

Sources & evidence

ORD record
ord-3ab74cde0a84460cb49a668c26764589
Source dataset
uspto-grants-2008_07
Patent number
US07396890B2

Reaction notes

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