Propylene Oxide → Phosphinothricin

HRID 1649947

Reaction equation

HRID 1649947 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][CH2:4][P:5](Cl)([CH3:7])=[O:6].C1[O:15]C1C>C(O)C.O>[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][CH2:4][P:5]([CH3:7])(=[O:15])[OH:6]

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 131716369L-homoalanin-4-yl(methyl)phosphinic acid chloride

Product 1

HCID 91619PhosphinothricinYield 81%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

0.33 g (0.0015 mol) of L-homoalanin-4-yl(methyl)phosphinic acid chloride are dissolved in 15 ml of ethanol/water and mixed with 0.3 g (0.005 mol) of propeneoxide. After allowing to stand for one day at room temperature, 0.22 g (80.1% of theory) of L-homoalanin-4-yl(methyl)phosphinic acid is obtained as a white solid with a melting point of 212°-214° C. (decomposes); [α]D22 =14.7° (c=0.984 in H2O).

Sources & evidence

ORD record
ord-05f7d902e8094cac854a65d79dea64e9
Source dataset
uspto-grants-1990_05
Patent number
US04922006

Linked notes

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