1,4-Dioxane hydrochloride → Ethyl 4-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinate hydrochloride

HRID 1525278Notes

Reaction equation

HRID 1525278 reaction equation
CC(C)([S@]([NH:6][C@H:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([P:14]([CH3:19])(=[O:18])[O:15][CH2:16][CH3:17])=[CH:10][CH:9]=1)=O)C.[ClH:27].O1CCOCC1>>[ClH:27].[NH2:6][C@H:7]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:8]1[CH:9]=[CH:10][C:11]([P:14]([CH3:19])(=[O:18])[O:15][CH2:16][CH3:17])=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117702199Ethyl 4-((R)-((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate2×

Product 1

HCID 89462726Ethyl 4-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinate hydrochlorideYield 91%

Procedure

Ethyl 4-((R)—((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate, 23-b, (9.5 g, 24.1 mmol) was dissolved in HCl/dioxane (100 ml) and the mixture was stirred at room temperature overnight. Then it was concentrated under vacuum and the residue was washed with ethyl acetate to provide the product, 23-c, (7.16 g, 91%).

Workup

  1. concentrationThen it was concentrated under vacuum
  2. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-b74a81436dab4c4e9e3e6fc1f426b076
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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