Triacetoxyperiodinane → Sar-114137

HRID 1796160ノート

反応式

HRID 1796160 の反応式
[OH:1][CH:2]([C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1)[C@@H:3]([NH:6][C:7](=[O:26])[CH:8]([CH2:18][S:19]([CH2:22][CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:20])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[CH2:4][CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:25][CH:23]([CH3:24])[CH2:22][S:19]([CH2:18][CH:8]([CH2:9][C:10]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[O:11])[C:7]([NH:6][C@H:3]([C:2]([C:27]1[N:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:29][N:28]=1)=[O:1])[CH2:4][CH3:5])=[O:26])(=[O:20])=[O:21]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 11635192N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide

生成物 1

HCID 9828551Sar-114137

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of N-{(S)-1-[Hydroxy-(5-phenyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-2-(2-methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-butyramide (41 mg, 0.076 mmol) in methylene chloride (6 mL) was treated with Dess-Martin periodinane (39 mg, 0.092 mmol) and stirred at room temperature for 90 minutes. The reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated aqueous bicarbonate solution and water, dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give 2-(2-Methyl-propane-1-sulfonylmethyl)-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-phenyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide as an off white solid (18 mg) (mixture of diastereoisomers).

後処理

  1. washThe reaction mixture was washed with a solution of Na2S2O3 in water (0.26M), saturated aqueous bicarbonate solution and water
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. washeluting with a mixture of ethyl acetate and heptane

出典と根拠

ORDレコード
ord-8f2cf64a27df4753ae152ad9be28f2cc
出典データセット
uspto-grants-2006_04
特許番号
US07030116B2

反応ノート

読み込み中…