Formaldehyde → (S)-benzyl 4-(3-(1,3-dioxoisoindolin-2-yl)propyl)-5-oxooxazolidine-3-carboxylate

HRID 409812

반응식

HRID 409812 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:6]([OH:8])=[O:7].[O:20]=[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])N1C(OCC)=O.C=O.[CH3:38]C1C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1.CCOC(C)=O.C1(C)C=CC=CC=1.CCOCC>[O:20]=[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23](=[O:30])[N:1]1[CH2:2][CH2:3][CH2:4][C@H:5]1[C:6](=[O:8])[O:7][CH2:38][N:9]1[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

참가 물질

9

반응물 4

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 31187N-CarbethoxyphthalimideHCID 7010490N-alpha-Benzyloxycarbonyl-L-ornithine

생성물 1

HCID 54380156(S)-benzyl 4-(3-(1,3-dioxoisoindolin-2-yl)propyl)-5-oxooxazolidine-3-carboxylate수율 76%

시약·촉매·용매 4

HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

(S)-5-amino-2-(benzyloxycarbonylamino)pentanoic acid (10.0 g, 37.56 mmol) and ethyl 1,3-dioxoisoindoline-2-carboxylate (9.04 g, 41.28 mmol) in NMP (40.0 mL) were heated to 150° C. for 30 min in 4 microwave reaction tubes. The mixture was diluted with EtOAc (500 mL). The organic mixture was washed with water (100 mL×2) and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give an oil, which was redissolved in toluene. To the resulting solution were added paraformaldehyde, PTSA and molecular sieves (3 A) and the mixture was heated to 150° C. for 20 min in a microwave reactor. The reaction mixture was diluted with ether (800 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel using a mixture of EtOAc and hexanes to give (S)-benzyl 4-(3-(1,3-dioxoisoindolin-2-yl)propyl)-5-oxooxazolidine-3-carboxylate (11.6 g, 76% for 2 steps).

후처리

  1. washThe organic mixture was washed with water (100 mL×2) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil, which
  6. washwashed with NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified on silica gel using
  11. additiona mixture of EtOAc and hexanes

출처 및 근거

ORD 기록
ord-8dfdc3cb80874c57b1b82ff6040b4b5a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759374B2

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