Tetrahydrofuran → N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamide

HRID 601987Notes

Reaction equation

HRID 601987 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([O:21][CH3:22])[C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH:23]1([C@@H:29]([NH2:31])[CH3:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:23]1([C@@H:29]([NH:31][C:11](=[O:12])[C:10]2[CH:9]=[C:8]([O:7][CH3:6])[C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH3:30])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5325951(S)-(+)-1-CyclohexylethylamineHCID 574456693,5-Dimethoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701188N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamideYield 81.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5 ml of THF and 0.38 g of 3,5-dimethoxy-4-(2-propynyloxy)benzoyl chloride were added 0.21 g of (1S)-1-(cyclohexyl)ethylamine and 0.23 g of triethylamine in order at room temperature. The mixture obtained was stirred at room temperature for 4 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.42 g of N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3,5-dimethoxybenzamide (hereinafter, described as the compound 23 of the present invention) represented by the formula:

Workup

  1. customThe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-37d67e90bc8147868db054ec37315321
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

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