Triacetoxyperiodinane → 4-Oxo-2-benzylsulfonylmethyl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-pyrrolidin-1-yl-butyramide

HRID 1830188노트

반응식

HRID 1830188 반응식
[OH:1][CH:2]([C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1)[CH:3]([NH:6][C:7](=[O:28])[CH:8]([CH2:17][S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])[CH2:9][C:10](=[O:16])[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:4][CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[O:16]=[C:10]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:9][CH:8]([CH2:17][S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])[C:7]([NH:6][CH:3]([C:2]([C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1)=[O:1])[CH2:4][CH3:5])=[O:28]

참가 물질

4

반응물 3

HCID 159087TriacetoxyperiodinaneHCID 22054105N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramideHCID 22607107sodium thiosulfate NaHCO3

생성물 1

HCID 101662494-Oxo-2-benzylsulfonylmethyl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-pyrrolidin-1-yl-butyramide

실험 절차

This amide was treated with Dess-Martin periodinane (222.7 mg, 0.45 mmol) at room temperature. After stirring for 1 hour, 5 mls of saturated Na2S2O3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 102 mg of 4-Oxo-2-benzylsulfonylmethyl-N-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-pyrrolidin-1-yl-butyramide; H1NMR (DMSO-d): 9.0–8.85(3H, m), 8.1–8(2H, m), 7.44–7.3(5H, m), 5.05–4.9(1H, m), 4.55–4.35(2H, m), 3.4–3.(8H, m), 2.6–2.4(1H, m), 2.05–1.9(1H, m), 1.9–1.6(5H, m), 0.96(3H, t); MS: 552.6(M−1), 554.6(M+1).

후처리

  1. waitAfter a further 0.5 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

출처 및 근거

ORD 기록
ord-244ca0144d94468bb1d5ad86cf8f3c52
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064123B1

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