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

HRID 1525254Notes

Reaction equation

HRID 1525254 reaction equation
CC(C)([S@]([NH:6][C@H:7]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[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:28].O1CCOCC1>>[ClH:28].[NH2:6][C@H:7]([C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=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

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 117702209Ethyl 4-((R)-((R)-1,1-dimethylethylsulfinamido)(4-fluorophenyl)methyl)phenyl(methyl)phosphinate

Product 1

HCID 117702271Ethyl 4-((R)-amino(4-fluorophenyl)methyl)phenyl(methyl)phosphinate hydrochlorideYield 80%

Procedure

Ethyl 4-((R)—((R)-1,1-dimethylethylsulfinamido)(4-fluorophenyl)methyl)phenyl(methyl)phosphinate, 18-d, (7 g, 18 mmol) was dissolved in HCl/dioxane (50 ml) and the mixture was stirred at room temperature for about 3 h. The mixture was then concentrated under vacuum and the residue was washed with ethyl acetate to provide the product, 18-e, (4.4 g, 80%).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-99c0f10db39c442da2aeed3d6487f204
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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