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

HRID 1400015
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HRID 1400015 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-6c4a2921fd73400fb15a025e53bd257e
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906914B2

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