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

HRID 1402663Notes

Reaction equation

HRID 1402663 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 L, 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-5a98a95deb2540f189235e8d6c30370a
Source dataset
uspto-grants-2014_12
Patent number
US08912148B2

Reaction notes

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