Formic Acid → Fosmidomycin

HRID 2052007Notes

Reaction equation

HRID 2052007 reaction equation
[OH:1][NH:2][CH2:3][CH2:4][CH2:5][P:6](=[O:9])([OH:8])[OH:7].[C:10](OC(=O)C)(=[O:12])C.C(O)=O.[OH-].[Mg+2].[OH-]>O>[CH:10]([N:2]([CH2:3][CH2:4][CH2:5][P:6](=[O:8])([OH:7])[OH:9])[OH:1])=[O:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 73981Magnesium HydroxideHCID 3421703-(Hydroxyamino)propylphosphonic acid

Product 1

HCID 572FosmidomycinYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An oily 3-(N-formyl-N-hydroxyamino)propylphosphonic acid (12.05 g.), which was prepared by the reaction of 3-(N-hydroxyamino)propylphosphonic acid (15.5 g.), acetic anhydride (12.3 g.) and formic acid (9.8 ml.) conducted in substantially the same manner as that of Example (31), was dissolved in water (80 ml.) and treated with magnesium hydroxide (5.83 g.) for 15 minutes under ice-cooling with stirring.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-62e0531f603544e8818ebff1f23c9af7
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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