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Sulfuric acid magnesium salt (1:1) → 1,5-anhydro-2,4-dideoxy-2-(6-(4-methoxybenzyl)-4,5-dimethyl-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pentitol

HRID 629419
ノート
印刷プレビュー

反応式

HRID 629419 の反応式
[CH:1]([C:3]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:9][C:4]=1[C:5](OC)=[O:6])=O.[NH2:24][C@@H:25]1[C@@H:30]([OH:31])[CH2:29][CH2:28][O:27][CH2:26]1.S([O-])([O-])(=O)=O.[Mg+2]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:10]2[CH:9]=[C:4]3[C:3]([CH2:1][N:24]([C@@H:25]4[C@@H:30]([OH:31])[CH2:29][CH2:28][O:27][CH2:26]4)[C:5]3=[O:6])=[C:12]([CH3:13])[C:11]=2[CH3:14])=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 55285677(3S,4S)-3-Aminotetrahydro-2H-pyran-4-OLHCID 118468425Methyl 2-formyl-5-(4-methoxybenzyl)-3,4-dimethylbenzoate

生成物 1

HCID 1184681511,5-anhydro-2,4-dideoxy-2-(6-(4-methoxybenzyl)-4,5-dimethyl-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-L-threo-pentitol収率 5.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of methyl 2-formyl-5-(4-methoxybenzyl)-3,4-dimethylbenzoate (13.5 g) in THF (270 mL) were added (3S,4S)-3-aminotetrahydro-2H-pyran-4-ol (5.06 g) and anhydrous magnesium sulfate (9.99 g), and the mixture was stirred at room temperature for 5 hr. The insoluble substance was removed by filtration, and the filtrate was concentrated. The residue was diluted with methanol (220 mL)-THF (250 mL), sodium triacetoxyborohydride (18.3 g) was added thereto, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, the mixture was washed with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The resulting solid was washed with ethyl acetate to give the crude title compound (6.4 g). The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.85 g). The crude title compound and the title compound purified by column were combined, and recrystallized from ethanol to give the title compound (6.48 g).

後処理

  1. customThe insoluble substance was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with methanol (220 mL)-THF (250 mL), sodium triacetoxyborohydride (18.3 g)
  4. additionwas added
  5. stirringthe mixture was stirred at room temperature for 15 hr
  6. additionThe reaction mixture was diluted with ethyl acetate
  7. washthe mixture was washed with water and saturated brine
  8. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. washThe resulting solid was washed with ethyl acetate
  11. customto give the crude title compound (6.4 g)
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-024e079b704347a08597a6dc64817fff
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315458B2

反応ノート

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