tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate → tert-Butyl(3S,4R)-3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate

HRID 338112ノート

反応式

HRID 338112 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[C:10]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([N:11]([C:16](=[S:26])[NH:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Zn].C(O)(=O)C>[C:18]([NH:17][C:16]([NH:11][C@:10]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:14]([CH2:13][OH:12])[CH2:15][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[S:26])(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

4

反応物 1

HCID 86697923tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

生成物 1

HCID 86697927tert-Butyl(3S,4R)-3-(benzoylcarbamothioylamino)-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate収率 70%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

反応条件

温度
40 °C

実験手順

A mixture of tert-butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (2.3 g, 5.1 mmol), acetic acid (20 mL), and powdered zinc (3.3 g, 50 mmol) is vigorously stirred at 40° C. for 1 hour, followed by an additional hour at 45-50° C. The reaction is concentrated under reduced pressure. To the residue is added diatomaceous earth and water, followed by a saturated solution of sodium bicarbonate. The mixture is filtered and washed with ethyl acetate. The filtrate is extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound (1.6 g, 70%). ES/MS (m/e): 456 (M+H).

後処理

  1. waitfollowed by an additional hour at 45-50° C
  2. concentrationThe reaction is concentrated under reduced pressure
  3. additionTo the residue is added diatomaceous earth and water
  4. filtrationThe mixture is filtered
  5. washwashed with ethyl acetate
  6. extractionThe filtrate is extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a residue
  11. customThe residue is purified by silica gel flash chromatography
  12. washeluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1)

出典と根拠

ORDレコード
ord-4002cef1fd194ff6abab01ec3c3a7e41
出典データセット
uspto-grants-2014_11
特許番号
US08889856B2

反応ノート

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