1-Aminocyclopropane-1-carboxylic acid → HCID 90224845, compound

HRID 1487100Notes

Reaction equation

HRID 1487100 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:10].[NH2:11][C:12]1([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CC(N(C)C)=O.[Cu](I)I>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([NH:11][C:12]2([C:15]([OH:17])=[O:16])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 207480372-Bromo-5-iodo-1,3-dimethylbenzeneHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 90224845HCID 90224845, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-5-iodo-1,3-dimethylbenzene (300 mg, 0.965 mmol), 1-aminocyclopropane carboxylic acid (195 mg, 1.93 mmol), copper iodide (I) (37 mg, 0.194 mmol), and diazabicycloundecene (0.50 mL, 3.35 mmol) in dimethylacetamide (2.6 mL) was stirred at 120° C. for three hours under nitrogen atmosphere. The reaction mixture was purified by silica gel column chromatography (Wakosil C18, acetonitrile-water (0.1% formic acid)) to afford 1-((4-bromo-3,5-dimethylphenyl)amino)cyclopropane carboxylic acid (219 mg, 80%).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (Wakosil C18, acetonitrile-water (0.1% formic acid))

Sources & evidence

ORD record
ord-6a30c01b46a547c7ab7b3a1a7fa23fd8
Source dataset
uspto-grants-2016_08
Patent number
US09428505B2

Reaction notes

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