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

반응식

[OH:1][CH:2]([C:29]1[O:30][C:31]([CH2:34][O:35][CH3:36])=[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+]>>[CH3:36][O:35][CH2:34][C:31]1[O:30][C:29]([C:2]([CH:3]([NH:6][C:7](=[O:28])[CH:8]([CH2:17][S:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:19])[CH2:9][C:10](=[O:16])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:4][CH3:5])=[O:1])=[N:33][N:32]=1

참가 물질

반응물 3

HCID 159087Triacetoxyperiodinane

HCID 22054041N-{1-[Hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide

HCID 22607107sodium thiosulfate NaHCO3

생성물 1

HCID 22054080n-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide

실험 절차

This amide was treated with Dess-Martin periodinane (114 mg, 0.153 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 17 mg of N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramide; H1 NMR(CDCl3): 8.2, 8(1H, d,d, NH, diastereomeric), 7.6–7.2(5H, m), 5.3–5.1(1H, m), 4.6(2H, s, OCH2), 4.3–4.1(3H, m), 3.8–3.2(9H, m), 3–2.4(2H, m), 2.2–1.4(6H, m), 0.95(3H, t); MS:519.6(M−1), 521.6(M+1).