Triacetoxyperiodinane → Sar-114137

HRID 1796160노트

반응식

HRID 1796160 반응식
[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]

참가 물질

4

반응물 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

생성물 1

HCID 9828551Sar-114137

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f2cf64a27df4753ae152ad9be28f2cc
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030116B2

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