Ethyl 3-((R)-((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate → Ethyl 3-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinate

HRID 1525283Notes

Reaction equation

HRID 1525283 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:9]=[C:10]([P:14]([CH3:19])(=[O:18])[O:15][CH2:16][CH3:17])[CH:11]=[CH:12][CH:13]=1)=O)C>Cl.O1CCOCC1>[NH2:6][C@H:7]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:8]1[CH:9]=[C:10]([P:14]([CH3:19])(=[O:18])[O:15][CH2:16][CH3:17])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 117702161Ethyl 3-((R)-((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate

Product 1

HCID 89462476Ethyl 3-((R)-amino(phenyl)methyl)phenyl(methyl)phosphinateYield 74%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Ethyl 3-((R)—((R)-1,1-dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate, 24-d, (15 g, 80% purity, 32.3 mmol) was dissolved in HCl/dioxane (70 ml, 4 mol/L) and the mixture was stirred at room temperature for 2 h. The mixture was concentrated under vacuum and the residue was dissolved with H2O (90 ml) and HCl (10 ml). The aqueous phase was extracted with EA (80 ml*5). The pH of the aqueous layer was adjusted to about pH=12 and extracted with EA (100 ml*3). The organic was dried over Na2SO4 and the crude product was purified with column (DCM/MeOH=100/1˜30/1) to provide the product, 24-e, (6.77 g, 74%).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved with H2O (90 ml) and HCl (10 ml)
  3. extractionThe aqueous phase was extracted with EA (80 ml*5)
  4. extractionextracted with EA (100 ml*3)
  5. dry with materialThe organic was dried over Na2SO4
  6. customthe crude product was purified with column (DCM/MeOH=100/1˜30/1)

Sources & evidence

ORD record
ord-948f7513469445018291c04ae896c867
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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