Diisopropylethylamine → 3-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

HRID 2111521Notes

Reaction equation

HRID 2111521 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:30])[CH2:10][CH2:11][CH2:12][C:13](=[O:29])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26])=[CH:17][CH:16]=1.[C:31]([O:35][C:36](=[O:49])[CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][NH2:48])([CH3:34])([CH3:33])[CH3:32].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:31]([O:35][C:36](=[O:49])[CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][NH:48][C:9](=[O:30])[CH2:10][CH2:11][CH2:12][C:13](=[O:29])[NH:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23](=[O:28])[CH2:24][C:25](=[O:27])[CH3:26])=[CH:19][CH:20]=1)([CH3:32])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 16218573tert-Butyl 12-amino-4,7,10-trioxadodecanoateHCID 576387144-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

Product 1

HCID 670685163-{2-[2-(2-{4-[4-(3,5-Dioxo-hexyl)-phenylcarbamoyl]-butyrylamino}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[4-(3,5-dioxo-hexyl)-phenylcarbamoyl]-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester (1.5 g, 3.6 mmol), 3-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (1.0 g, 3.6 mmol) and DIEA (1.3 μL, 7.2 mmol) in CH2Cl2 (10 mL) was stirred at rt overnight. The solvent was removed in vacuo and the residual oil purified using column chromatography EtOAc/MeOH (95:5) to give the title compound as a transparent oil, (M+1)=579.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residual oil purified

Sources & evidence

ORD record
ord-fc5432ec5f3843faa7ed05d61ce280f3
Source dataset
uspto-grants-2009_04
Patent number
US07521425B2

Reaction notes

Loading…