Acetone → HCID 86607366, compound

HRID 646450Notes

Reaction equation

HRID 646450 reaction equation
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])(=[O:5])[C:2]([CH3:4])=[CH2:3].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].CC(C)=[O:25]>>[OH:25][N:6]([C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22])[C:12]([OH:14])=[O:13]

Participants

4

Reactant 3

HCID 180AcetoneHCID 80170N-HydroxysuccinimideHCID 1009776-((2-Methyl-1-oxoallyl)amino)hexanoic acid

Product 1

HCID 86607366HCID 86607366, compoundYield 81%

Procedure

N-methacryloyl-6-aminocaproic acid (3.98 g, 20 mmol) was dissolved in 50 ml of acetone, and then to this solution 1,3-dicyclohexlylcarbodiimide (4.5 g, 22 mmol) and N-hydroxysuccinimide (2.55 g, 22 mmol) were added. Resulting mixture was stirred at room temperature for 6 hours. The reaction was quenched by addition of 1 ml of water, the precipitate of 1,3-dicyclohexylurea was removed by filtration and washed with acetone. The solution was concentrated in vacuum and purified by column chromatography on silica gel using step gradient of acetone (0-5%) in chlorophorm to give activated ester (3, Met=b, n=2) with yield 81% (4.8 g). MALDI MS: found 296.1, C14H20N2O5, calc. 296.09.

Workup

  1. customResulting mixture
  2. customThe reaction was quenched by addition of 1 ml of water
  3. customthe precipitate of 1,3-dicyclohexylurea was removed by filtration
  4. washwashed with acetone
  5. concentrationThe solution was concentrated in vacuum
  6. custompurified by column chromatography on silica gel using step gradient of acetone (0-5%) in chlorophorm

Sources & evidence

ORD record
ord-b05e92e55d164afba0fda2093dcb819d
Source dataset
uspto-grants-2010_04
Patent number
US07705136B2

Reaction notes

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