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Sodium Bisulfite → (2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid

HRID 627196
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HRID 627196 반응식
[CH2:1]([O:4][N:5]([CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][Si](C(C)(C)C)(C)C)[CH:20]=[C:19]1[CH2:40][C:41]([NH2:43])=[O:42])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].I([O-])(=O)(=O)=[O:45].[Na+].OS([O-])=O.[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]([CH:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C@H:21]([C:31]([OH:45])=[O:32])[CH:20]=[C:19]1[CH2:40][C:41]([NH2:43])=[O:42])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]
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참가 물질

6

반응물 3

HCID 23665763Sodium BisulfiteHCID 23667635Sodium periodateHCID 89852098(2S)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate2회

생성물 1

HCID 89851815(2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid

시약·촉매·용매

2
HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To the solution of (25)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 174, 2.61 g, 4.96 mmol) in acetonitrile (50 mL) was added sodium periodate (4.66 g, 21.81 mmol) and catalytic solution of NaCr2O7/HNO3 solution (6.0 mL) at room temperature and stirred for 15 h. The mixture was diluted with 100 mL ethyl acetate, 25 mL 1M pH 7 buffer, 25 mL 2M NaHSO3. The aqueous solution was extracted with 50 mL ethyl acetate. The ethyl acetate layer was then washed with brine and dried over MgSO4, filtered and concentrated to afford (2S)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-(2-amino-2-oxoethyl)-1-(tert-butoxycarbonyl)-1,2,5,6-tetrahydropyridine-2-carboxylic acid, which was used directly in the next step without further purification. Pale yellow solid, crude, 2.79 g, 104%.

후처리

  1. extractionThe aqueous solution was extracted with 50 mL ethyl acetate
  2. washThe ethyl acetate layer was then washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eff4b0268d6841a9a1d2a0d7208e1a21
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309245B2

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