4-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid → 3-[4-[5-Cyano-2-(2-hydroxyethylamino)phenylcarbamoylmethoxy]phenoxy]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 412553Notes

Reaction equation

HRID 412553 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][OH:13])[C:5]#[N:6].[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([O:26][C:27]2[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=2)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33](=[O:34])[NH:1][C:2]3[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=3[NH:10][CH2:11][CH2:12][OH:13])=[CH:36][CH:37]=2)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 185363434-(1-Tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acidHCID 185364343-Amino4-(2-hydroxyethylamino)benzonitrile

Product 1

HCID 696974193-[4-[5-Cyano-2-(2-hydroxyethylamino)phenylcarbamoylmethoxy]phenoxy]pyrrolidine-1-carboxylic acid tert-butyl esterYield 75.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-amino-4-(2-hydroxyethylamino)benzonitrile (1.21 g) and 4-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)phenoxyacetic acid (2.30 g) in chloroform (50 ml) was added 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroxyquinoline (2.19 g), and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to give the title compound (2.56 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-479ec4dad8e14a0ba282c76192ca851c
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…