6-Aminohexanoic Acid → 6-((2-Methyl-1-oxoallyl)amino)hexanoic acid

HRID 646449Notes

Reaction equation

HRID 646449 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10](OC(=O)C)(=[O:14])[C:11]([CH3:13])=[CH2:12]>>[C:10]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

3

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 13878871HCID 13878871, compound

Product 1

HCID 1009776-((2-Methyl-1-oxoallyl)amino)hexanoic acidYield 87%

Procedure

To a solution of 6-aminocaproic acid (6.55 g), 50 mmol) in 150 ml of glacial acetic acid methacrylic anhydride (8.7 ml, 55 mmol) were added at room temperature, and resulting mixture was stirred for 12 hours. All volatiles were removed under reduced pressure. Crude material was submitted to column chromatography on silica gel, which was performed in chloroform with applying gradient of methanol (0-7.5%) and gave 8.65 g (87%) of N-methacryloyl-6-aminocaproic acid as white solid. MALDI MS: found 200.06 (M+H)+, C10H17NO3; calc. 199.07.

Workup

  1. customresulting mixture
  2. customAll volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-becaeb7442de40c99328f7a6719b7574
Source dataset
uspto-grants-2010_04
Patent number
US07705136B2

Reaction notes

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