Hydrochloric Acid → 5-azidopentanoic Acid

HRID 386422Notes

Reaction equation

HRID 386422 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])=[N+:2]=[N-:3].CN(C)C=O.[OH-].[Li+].Cl>O>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[N+:2]=[N-:3]

Participants

6

Conditions

Temperature
25 °C

Procedure

To ethyl 5-azidovalerate (1.6 g; 10 mmol; Example 2.1) in 5 ml-dimethylformamide, was added lithium hydroxide (1.0 g; 20 mmol; Fisher) in 5 ml water, and the reaction mixture was stirred 12 h at 25° C. The reaction mixture was adjusted to pH ˜4 by addition of 1 N HCl and was extracted with 100 ml diethyl ether. The resulting organic layer was washed with water (100 ml) and brine (100 ml), dried over sodium sulfate, and dried in vacuo. Yield: 1.4 g (9.8 mmol, 99% yield).

Workup

  1. extractionwas extracted with 100 ml diethyl ether
  2. washThe resulting organic layer was washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried over sodium sulfate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5ca6025cb0c84ab8afc1e58f3fb6d681
Source dataset
uspto-grants-2013_02
Patent number
US08372839B2

Reaction notes

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