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

HRID 1830188ノート

反応式

HRID 1830188 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-244ca0144d94468bb1d5ad86cf8f3c52
出典データセット
uspto-grants-2006_06
特許番号
US07064123B1

反応ノート

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