Potassium Hydroxide → 3-[(Dibenzylamino)oxy]propanoic acid

HRID 979261Notes

Reaction equation

HRID 979261 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>O1CCCC1.O>[CH2:16]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21621270HCID 21621270, compound

Product 1

HCID 235038743-[(Dibenzylamino)oxy]propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 22.4 g of methyl 3-[N,N-dibenzylaminoxy]propanoate and 4.50 g of potassium hydroxide in 200 ml of tetrahydrofuran and 200 ml of water is heated under reflux for 12 hours under N2. The mixture is concentrated under reduced pressure and the residue is partitioned between water and ether. The combined aqueous extracts are acidified with hydrochloric acid and then extracted with methylene chloride. The combined organic extracts are dried (MgSO4) and evaporated under reduced pressure to afford the title compound as a pale yellow oil.

Workup

  1. temperatureunder reflux for 12 hours under N2
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is partitioned between water and ether
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic extracts are dried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c4040b9dd1044af0b6ee41a257c75a4d
Source dataset
uspto-grants-1987_05
Patent number
US04666962

Reaction notes

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