Ethyl 3-((S)-((S)-1,1dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate → HCID 89462355, compound

HRID 1525288Notes

Reaction equation

HRID 1525288 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 117701946Ethyl 3-((S)-((S)-1,1dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate2×

Product 1

HCID 89462355HCID 89462355, compound

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Ethyl 3-((S)—((S)-1,1dimethylethylsulfinamido)(phenyl)methyl)phenyl(methyl)phosphinate, 25-c, (25 g, 76% purity, 48.7 mmol) was dissolved in HCl/dioxane (150 ml, 4 mol/L) and the mixture was stirred at room temperature for 2 h. The mixture was then concentrated under vacuum and the residue was dissolved in H2O (90 ml) and HCl (10 ml). The aqueous phase was extracted with EA (80 ml×5). The pH of the aqueous phase was adjusted to about pH=12 and extracted with EA (100 ml*3). The organic layer was dried over Na2SO4. The solvent was removed to provide crude product, 25-d, (10.55 g) and the crude product was used for the next step directly.

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. dissolutionthe residue was dissolved in H2O (90 ml)
  3. extractionThe aqueous phase was extracted with EA (80 ml×5)
  4. extractionextracted with EA (100 ml*3)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customThe solvent was removed
  7. customto provide crude product, 25-d, (10.55 g)

Sources & evidence

ORD record
ord-04e65857d7ac41008fe5dd28c924e037
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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