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Tetrahydrofuran → N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3-methoxybenzamide

HRID 601985
Notes
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Reaction equation

HRID 601985 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]#[CH:20])[C:11](Cl)=[O:12].[CH:21]1([C@@H:27]([NH2:29])[CH3:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH:21]1([C@@H:27]([NH:29][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]#[CH:20])=[C:8]([O:7][CH3:6])[CH:9]=2)[CH3:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5325951(S)-(+)-1-CyclohexylethylamineHCID 574456713-Methoxy-4-(2-propynyloxy)benzoyl chloride

Product 1

HCID 57701156N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3-methoxybenzamideYield 78.3%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of 10 ml of THF and 0.30 g of 3-methoxy-4-(2-propynyloxy)benzoyl chloride were added 0.21 g of (1S)-1-(cyclohexyl)ethylamine and 0.20 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 washed with methyl tert-butyl ether and hexane to obtain 0.33 g of N-((1S)-1-cyclohexylethyl)-4-(2-propynyloxy)-3-methoxybenzamide (hereinafter, described as the compound 21 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
  4. washThe residue was washed with methyl tert-butyl ether and hexane

Sources & evidence

ORD record
ord-975a8bbb487b43fa81581330c690b362
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902400B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes