tert-Butanol → (R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

HRID 1160252

反応式

HRID 1160252 の反応式
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:40]CC1.C(O)(C)(C)C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=[O:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 66671784(R)-4-benzyl-3-[(S)-2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one

生成物 1

HCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde収率 48%

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒

実験手順

Treat a mixture of (R)-4-benzyl-3-[(S)2-(4-benzyloxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (0.96 g, 1.8 mmol), THF (21 mL) and water (7 mL) with 2.5% osmium tetroxide in t-butanol (46 mg, 0.18 mmol). Add sodium periodate (1.17 g, 5.5 mmol) and stir the reaction 4 hr at room temperature. Quench the reaction with water and extract with ethyl acetate. Wash the organic phase with aqueous 1N sodium thiosulfate then brine. Dry the organic layer over magnesium sulfate, filter, and concentrate under vacuum. Purify the crude material by silica gel chromatography using hexanes:ethyl acetate to elute the pure product. Concentrate the fractions containing product under vacuum to afford 0.46 g (48%) of desired product. MS (m/z): 526 (M+).

後処理

  1. additionTreat
  2. customthe reaction 4 hr at room temperature
  3. customQuench
  4. customthe reaction with water
  5. extractionextract with ethyl acetate
  6. washWash the organic phase with aqueous 1N sodium thiosulfate
  7. dry with materialDry the organic layer over magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum
  10. customPurify the crude material by silica gel chromatography
  11. washethyl acetate to elute the pure product
  12. concentrationConcentrate the fractions
  13. additioncontaining product under vacuum

出典と根拠

ORDレコード
ord-0711713827cf439ba42821039cd9de74
出典データセット
uspto-grants-2010_10
特許番号
US07816349B2

関連ノート

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