Tetrahydrofuran → HCID 22643281、化合物

HRID 1166578ノート

反応式

HRID 1166578 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH:34]=CC)=[C:20]([NH:23][C:24]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:25])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:37]1CCCC1>O.O=[Os](=O)(=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19]([CH:34]=[O:37])=[C:20]([NH:23][C:24]([O:26][CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:25])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 8028TetrahydrofuranHCID 86586522HCID 86586522、化合物

生成物 1

HCID 22643281HCID 22643281、化合物

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回

実験手順

To a solution {(2R)-7-{[(benzyloxy)carbonyl]amino}-8-[1-propenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl 4-methylbenzenesulfonate (4.5 g, 8.84 mmole) in tetrahydrofuran (225 mL) was added OsO4 (1.65 mL, 0.270 mmole). Then a solution of NalO4 (9.45 g, 44.2 mmole) in water (100 mL) was added dropwise. The reaction was stirred at room temperature under nitrogen overnight. Water (250 mL) was added to the mixture and it was then extracted with ethyl acetate. The organic phase was then washed with brine, dried over magnesium sulfate, filtered and evaporated to 4.45 g (>95%) of the (R)-enantiomer of the title compound as a yellow solid. 1H (CDCl3) broad singlet 10.8 δ (1H); singlet 10.1 δ (1H); doublet 7.9 δ (1H); doublet 7.8 δ (2H); multiplet 7.4 δ (7H); doublet 7.0 δ (1H); singlet 5.2 δ(2H); multiplet 4.5 δ (1H); multiplet 4.2 δ (3H); multiplet 4.1 6 δ (1H); singlet 2.4 δ (3H).

後処理

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic phase was then washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to 4.45 g (>95%) of the (R)-enantiomer of the title compound as a yellow solid

出典と根拠

ORDレコード
ord-66aad402d55840bb94d34a756a9df6ac
出典データセット
uspto-grants-2003_09
特許番号
US06613913B2

反応ノート

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