Tetrahydrofuran → N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694957ノート

反応式

HRID 1694957 の反応式
C(N(CC)CC)C.[CH:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([S:17](Cl)(=[O:19])=[O:18])=[CH:10][CH:9]=1.Cl.[NH2:22][C@H:23]([C@H:26]1[O:30][C:29](=[O:31])[C@H:28]([CH3:32])[CH2:27]1)[CH2:24][OH:25].O1CCCC1>O>[OH:25][CH2:24][C@H:23]([NH:22][S:17]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:13][C:12]=1[N+:14]([O-:16])=[O:15])(=[O:19])=[O:18])[C@@H:26]1[CH2:27][C@@H:28]([CH3:32])[C:29](=[O:31])[O:30]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66645577(3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride

生成物 1

HCID 66645672N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide収率 56%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

8.66 g of triethylamine (85.7 mmol) and 9.67 g of O-nitrobenzenesulfonyl chloride (41.3 mmol) were added to a solution of (3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride obtained in the above reaction in a mixed solvent of tetrahydrofuran (120 ml) and water (12.0 ml) at 0° C., and the mixture was stirred at the same temperature for two hours. The reaction mixture was concentrated under reduced pressure and 200 ml of water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:ethyl acetate). Further, 10 ml of diisopropyl ether and 20 ml of ethyl acetate were added, and the precipitated solid was collected by filtration to obtain 5.27 g of the title compound (total yield over two steps: 56%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 200 ml of water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThen, the organic layer was washed with water
  5. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (elution solvent:ethyl acetate)
  9. additionFurther, 10 ml of diisopropyl ether and 20 ml of ethyl acetate were added
  10. filtrationthe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-ded480ffa9fc4fa39f462a4d5849e77f
出典データセット
uspto-grants-2012_04
特許番号
US08158790B2

反応ノート

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