Water → 2,5-Pyrrolidinedione, 1-[(5-azido-1-oxopentyl)oxy]-

HRID 386423Notes

Reaction equation

HRID 386423 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[N+:2]=[N-:3].O[N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18].Cl.C(N=C=NCCCN(C)C)C.O>ClCCl>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18])=[O:9])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 111161715-azidopentanoic Acid

Product 1

HCID 111284002,5-Pyrrolidinedione, 1-[(5-azido-1-oxopentyl)oxy]-Yield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-azidovaleric acid (715 mg; 5 mmol; Example 2.2) and N-hydroxysuccinimide (632 mg; 5.5 mmol; Aldrich) in 30 ml dichloromethane, was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.05 g; 5.5 mmol; Aldrich), and the reaction was stirred 12 h at room temperature. To the reaction mixture, was added water (50 ml), and the separated organic phase was washed with water (100 ml) and brine (100 ml), dried over sodium sulfate, dried in vacuo. The product was purified via flash chromatography on silica gel (240-400 mesh) in 3:1 (v/v) hexane:ethyl acetate. Yield: 843 mg (3.5 mmol, 70% yield). M+H+: expected, 241.09.7; found, 241.03.

Workup

  1. washthe separated organic phase was washed with water (100 ml) and brine (100 ml)
  2. dry with materialdried over sodium sulfate
  3. customdried in vacuo
  4. customThe product was purified via flash chromatography on silica gel (240-400 mesh) in 3:1 (v/v) hexane

Sources & evidence

ORD record
ord-2bf04632125a46c98eab6b244e475aac
Source dataset
uspto-grants-2013_02
Patent number
US08372839B2

Reaction notes

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