Ethanol → HCID 19381505, compound

HRID 2209731Notes

Reaction equation

HRID 2209731 reaction equation
[C:1]([C:3]1[CH:37]=[CH:36][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:27]([N:29]([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])=[O:28])=[C:18]([CH:26]=2)[O:19][C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:5][CH:4]=1)#[N:2].Cl.[CH2:39](N=C=NCCCN(C)C)[CH3:40].OC1C2N=NNC=2C=CC=1.C(O)C>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:27]([N:29]([CH:30]([CH3:32])[CH3:31])[CH:33]([CH3:35])[CH3:34])=[O:28])=[C:18]([CH:26]=2)[O:19][C:20]([CH3:25])([CH3:24])[C:21]([O:23][CH2:39][CH3:40])=[O:22])=[CH:36][CH:37]=1)#[N:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19040993HCID 19040993, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 19381505HCID 19381505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2-[5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]-2-methylpropanoic acid (2.0 g, 4.0 mmol) in 50 mL of dichloromethane is treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (770 mg, 4.0 mmol), hydroxybenztriazole (540 mg, 4.0 mmol), and ethanol (220 mg, 4.8 mmol) and stirred at room temperature over 3 days. The reaction is concentrated in vacuo and purified by chromatography on silica gel (60 g) with 40-50% ethyl acetate/hexane as the eluent to afford ethyl 2-[5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]-2- methylpropanoate as a colorless foam.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. custompurified by chromatography on silica gel (60 g) with 40-50% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-dfce17cd5b764d72acc410c40245986d
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

Loading…