Hydrochloric Acid → 2-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinic acid

HRID 1776655노트

반응식

HRID 1776655 반응식
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][N:23]=1)[C:16]([O:18]CC)=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][N:23]=1)[C:16]([OH:18])=[O:17])[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89460062ethyl 2-(N-(tert-butoxycarbonyl)methyl-sulfonamido)isonicotinate

생성물 1

HCID 894600592-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinic acid수율 74%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of ethyl 2-(N-(tert-butoxycarbonyl)methylsulfonamido)isonicotinate (0.920 g, 2.67 mmol) in THF (15 ml), aqueous 1M LiOH (2.94 ml, 2.94 mmol) was added, and the reaction was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate and acidified with aqueous 2N HCl. The organic layer was separated, washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the solid residue was purified by trituration with iPr2O affording after filtration 2-(N-(tert-butoxycarbonyl)methylsulfonamido) isonicotinic acid as a white solid (0.625 g, 1.976 mmol, 74.0% yield, MS/ESI+ 339.2 [MNa]+).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum
  5. customthe solid residue was purified by trituration with iPr2O affording
  6. filtrationafter filtration 2-(N-(tert-butoxycarbonyl)methylsulfonamido) isonicotinic acid as a white solid (0.625 g, 1.976 mmol, 74.0% yield, MS/ESI+ 339.2 [MNa]+)

출처 및 근거

ORD 기록
ord-d2aa593904fd4f47a81a3d35efc731d8
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265768B2

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