Ammonium Chloride → (R,R)-2-methyl-propane-2-sulfinic acid [2-amino-1-(4-fluoro-phenyl)-ethyl]-amide

HRID 1400015Notes

Reaction equation

HRID 1400015 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH2:9][N+:10]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-]>[Zn].CC(C)=O.O>[NH2:10][CH2:9][C@H:8]([NH:13][S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66958061(R,R)-2-methyl-propane-2-sulfinic acid [1-(4-fluoro-phenyl)-2-nitro-ethyl]-amide

Product 1

HCID 66957899(R,R)-2-methyl-propane-2-sulfinic acid [2-amino-1-(4-fluoro-phenyl)-ethyl]-amideYield 89.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Zn powder (5.07 g, 77.6 mmol) was added to a solution of (R,R)-2-methyl-propane-2-sulfinic acid [1-(4-fluoro-phenyl)-2-nitro-ethyl]-amide (2.24 g, 7.76 mmol) and NH4Cl (4.15 g, 77.6 mmol) in 5:1 acetone/H2O (24 mL) at rt. After 10 min, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The crude residue was crystallized using CH2Cl2 (20 mL) and hexanes (50 mL) to provide (R,R)-2-methyl-propane-2-sulfinic acid [2-amino-1-(4-fluoro-phenyl)-ethyl]-amide (1.8 g, 89%). MS (ESI+): calcd for C12H19FN2OS m/z 258.12. found 259.1 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe crude residue was crystallized

Sources & evidence

ORD record
ord-6c4a2921fd73400fb15a025e53bd257e
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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