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 470237노트

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HRID 470237 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

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온도
40 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-609917e1ebae4ae19fee3c3d198b2dac
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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