HCID 54291210, compound → HCID 53739954, compound

HRID 376174Notes

Reaction equation

HRID 376174 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([CH2:18][P:19]([OH:22])([OH:21])=[O:20])=[CH:5][C@@H:6]([NH2:17])[C:7]([O:9]CC1C=CC=CC=1)=[O:8].[H][H]>O.[Pd]>[OH:1][CH2:2][CH2:3][C:4]([CH2:18][P:19]([OH:22])([OH:21])=[O:20])=[CH:5][C@@H:6]([NH2:17])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 54291210HCID 54291210, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53739954HCID 53739954, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2.5 g (7.59 mmol) of benzyl 6-hydroxy-2(R)-amino-4-phosphonomethyl-hex-3-enoate are dissolved in 35 ml of water and, after addition of 0.25 g of 10% palladium on charcoal, subjected to hydrogenolysis under normal pressure. When no more hydrogen is taken up, the catalyst is filtered off over diatomeic earth, and the filtrate is hydrophilized. 1.12 g (61% yield) of 6-hydroxy-2(R)-amino-4-phosphonomethyl-hex-3-enoic acid are thus obtained. ee=91%; αD -59° (c=1.0 H2O).

Workup

  1. filtrationthe catalyst is filtered off over diatomeic earth

Sources & evidence

ORD record
ord-667fced7d7dc4d83a59d6b868bb32e7f
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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