2-Amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid ethyl ester → 2-Amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid

HRID 487463Notes

Reaction equation

HRID 487463 reaction equation
C([O:3][C:4](=[O:18])[CH:5]([NH2:17])[CH:6]=[C:7]([CH2:12][P:13]([OH:16])([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][OH:11])C>O>[NH2:17][CH:5]([CH:6]=[C:7]([CH2:12][P:13]([OH:16])([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][OH:11])[C:4]([OH:18])=[O:3]

Participants

3

Reactant 1

HCID 545694002-Amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid ethyl ester

Product 1

HCID 542080662-Amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.1 g (3.9 mmol) of 2-amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid ethyl ester in 8 ml of water are stirred at 130° C. for 18 hours in a bomb tube. The dark reaction solution is treated with activated carbon and filtered over Hyflo®. The colourless filtrate is concentrated to ~3 ml, and ~25 ml of ethanol are added. The resulting suspension is filtered with suction and dried under a high vacuum at 50° C. 2-amino-7-hydroxy-4-phosphonomethyl-hept-3-enoic acid having a melting point from 190° C. and above (decomp.) is obtained.

Workup

  1. additionThe dark reaction solution is treated with activated carbon
  2. filtrationfiltered over Hyflo®
  3. concentrationThe colourless filtrate is concentrated to ~3 ml, and ~25 ml of ethanol
  4. additionare added
  5. filtrationThe resulting suspension is filtered with suction
  6. customdried under a high vacuum at 50° C

Sources & evidence

ORD record
ord-0aa8ee9fd73b465183f23dfe9b420629
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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