3-(5-Dimethylcarbamoyl-pentyl)-n-(2-hydroxy-1-methyl-ethyl)-benzamide → 3-(5-Dimethylcarbamoyl-pent-1-ynyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide

HRID 2271355Notes

Reaction equation

HRID 2271355 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[C:13]([NH:15][CH:16]([CH3:19])[CH2:17][OH:18])=[O:14])=[O:4].CN(C)C(CCCCCC1C=C(C=CC=1)C(NC(C)CO)=O)=O>>[CH3:23][N:2]([CH3:1])[C:3]([CH2:5][CH2:6][CH2:7][C:8]#[C:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[C:13]([NH:15][CH:16]([CH3:19])[CH2:17][OH:18])=[O:14])=[O:4]

Participants

3

Reactant 2

HCID 592602433-(5-Dimethylcarbamoyl-pentyl)-n-(2-hydroxy-1-methyl-ethyl)-benzamideHCID 671353913-(5-Dimethylcarbamoyl-pent-1-enyl)-n-(2-hydroxy-1-methyl-ethyl)benzamide

Product 1

HCID 113015293-(5-Dimethylcarbamoyl-pent-1-ynyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide

Procedure

The alkyne 8 (0.100 g, 0.3 mmol) was synthesized by Lindlar catalyzed reduction using method E to obtain a mixture of 16 and 3-(5-dimethylcarbamoyl-pentyl)-N-(2-hydroxy-1-methyl-ethyl)-benzamide (13) which were separated by reverse-phase HPLC chromatography (20% acetonitrile/80% water 20 min isocratic program) (16, 34 mg).

Workup

  1. customto obtain
  2. customwere separated by reverse-phase HPLC chromatography (20% acetonitrile/80% water 20 min isocratic program) (16, 34 mg)

Sources & evidence

ORD record
ord-a2776b1a25004a5f8e00241d048e3c0e
Source dataset
uspto-grants-2015_09
Patent number
US09120723B2

Reaction notes

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