Dicyclohexylamine → Dicyclohexylammonium 4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate

HRID 322891

Reaction equation

HRID 322891 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])#[N:2].[CH:31]1([NH:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(OCC)C>[C:1]([C:3]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[CH:19][C:4]=1[O:5][CH:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH2:7][CH2:8][C:9]([O-:11])=[O:10])#[N:2].[CH:38]1([NH2+:37][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1

Participants

4

Reactant 2

HCID 7582DicyclohexylamineHCID 220101494-(2-Cyano-5-(3-pyridylmethoxy)phenoxy)-4-(2-methylphenyl)butanoic acid

Product 1

HCID 22010329Dicyclohexylammonium 4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-[2-cyano-5-(3-pyridylmethoxy)-phenoxy]-4-(2-methylphenyl)butanoic acid, thought to be the (R)-enantiomer, (50 mg), dicyclohexylamine (0.5 mL) and diethyl ether (10 mL) is stirred at ambient temperature for 18 hours. The resulting precipitate is collected and washed with diethyl ether, to give dicyclohexylammonium 4-[2-cyano-5-(3-pyridylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate, thought to be the (R)-enantiomer, (30 mg) in the form of a white solid, m.p. 92-93° C.

Workup

  1. customThe resulting precipitate is collected
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-d77ef45c1c564a5cb061d24f48a0d56d
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Linked notes

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