Triethylamine → 2-Phenyl-cyclopropanecarboxylic acid(2-hydroxy-1-naphthalen-2-yl-ethyl)-amide

HRID 857028Notes

Reaction equation

HRID 857028 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)[CH2:3][OH:4].[C:15]1([CH:21]2[CH2:23][CH:22]2[C:24](O)=[O:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[OH:4][CH2:3][CH:2]([NH:1][C:24]([CH:22]1[CH2:23][CH:21]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:25])[C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 703232-Phenylcyclopropane-1-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 8027555(R)-2-Amino-2-(naphthalen-2-yl)ethanol

Product 1

HCID 218646822-Phenyl-cyclopropanecarboxylic acid(2-hydroxy-1-naphthalen-2-yl-ethyl)-amideYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (R)-2-amino-2-naphthalen-2-yl-ethanol (0.2 mmol), 2-phenyl-cyclopropanecarboxylic acid (0.2 mmol), EDAC.HCl (0.4 mmol), DMAP (0.2 mmol), and triethylamine (0.6 mmol) in dichloromethane (2 mL) was stirred at room temperature for 12 h. The reaction mixture was purified by flash chromatography eluting with 50% hexanes in ethyl acetate to give the desired product (52 mg) as a solid.

Workup

  1. customThe reaction mixture was purified by flash chromatography
  2. washeluting with 50% hexanes in ethyl acetate

Sources & evidence

ORD record
ord-a309c780d9f24f10a68d218b32a3221f
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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