HCID 10951162, compound → HCID 15480205, compound

HRID 989628Notes

Reaction equation

HRID 989628 reaction equation
[C:1]([O:5][P:6]([CH2:17][CH:18]([CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([CH2:8][NH:9]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:9][CH2:8][P:6]([CH2:17][CH:18]([CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7]

Participants

4

Reactant 1

HCID 10951162HCID 10951162, compound

Product 1

HCID 15480205HCID 15480205, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of di-tert-butyl 2-[((tert-butoxy)-{[benzylamino]methyl}phosphoryl)methyl]pentane-1,5-dioate (8.20 g, 16.5 mmol) in ethanol (100 mL) was added palladium on carbon (0.50 g), and the suspension was shaken under hydrogen (50 psi) for 4 days. The catalyst was removed by filtration through a pad of Celite. The filtrate was concentrated to give 6.629 g of colorless oil (99% yield): 1H NMR (CD3OD) δ 1.40-1.60 (m, 27H), 1.80-2.00 (m, 3H), 2.2-2.4 (m, 3H), 2.7-3.0 (m, 3H).

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-33d3da1b279e46548980c1d6627881a8
Source dataset
uspto-grants-2002_10
Patent number
US06458775B1

Reaction notes

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