5-Hexynoic acid → 6-[3-(2-Hydroxy-1-methyl-ethylcarbamoyl)phenyl]-hex-5-ynoic acid

HRID 2067165

Reaction equation

HRID 2067165 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](I)[CH:8]=1)[CH3:4].[C:15]([OH:22])(=[O:21])[CH2:16][CH2:17][CH2:18][C:19]#[CH:20]>>[OH:1][CH2:2][CH:3]([NH:5][C:6]([C:7]1[CH:8]=[C:9]([C:20]#[C:19][CH2:18][CH2:17][CH2:16][C:15]([OH:22])=[O:21])[CH:10]=[CH:11][CH:12]=1)=[O:14])[CH3:4]

Participants

3

Reactant 2

HCID 1430365-Hexynoic acidHCID 23730076N-(2-hydroxy-1-methyl-ethyl)-3-iodobenzamide

Product 1

HCID 113582156-[3-(2-Hydroxy-1-methyl-ethylcarbamoyl)phenyl]-hex-5-ynoic acidYield 99%

Procedure

The iodobenzamide (1) (2.00 g, 6.5 mmol) was coupled with 5-hexynoic acid using method B yielding (4) (1.87 g, 6.42 mmol; 99% yield).

Sources & evidence

ORD record
ord-c98b04fa696f45bbb0281eb92dc41755
Source dataset
uspto-grants-2012_10
Patent number
US08293796B2

Linked notes

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