Acetic Acid → tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}butanoyl)cyclopropanecarboxylate

HRID 1173610노트

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HRID 1173610 반응식
C(NC(C)C)(C)C.[CH:8]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]1.[CH2:18]([C@H:20]1[C:24](=O)[O:23]C(=O)[N:21]1[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH3:19].C(O)(=O)C>O1CCCC1.O>[CH2:30]([O:29][C:27]([NH:21][C@@H:20]([CH2:18][CH3:19])[C:24]([C:8]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]1)=[O:23])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 13676038tert-Butyl cyclopropanecarboxylateHCID 59557010benzyl (4S)-4-ethyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate

생성물 1

HCID 59556905tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}butanoyl)cyclopropanecarboxylate수율 24.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

A solution of diisopropylamine (3.76 mL) in tetrahydrofuran (50 mL) was cooled to −78° C., n-butyllithium-hexane solution (16.56 mL, 1.6 mol/L) was added dropwise and, after the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr. Subsequently, a solution of tert-butyl cyclopropanecarboxylate (3.77 g) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was further stirred at −78° C. for 30 min. A solution of benzyl(4S)-4-ethyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (3.49 g) in tetrahydrofuran (50 mL) was added dropwise at −78° C. for 30 min and the mixture was stirred at −78° C. for 30 min. Acetic acid was added to the reaction mixture at −78° C., water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→2/1) to give the title compound as a colorless oil (yield: 1.16 g, 24%).

후처리

  1. additionn-butyllithium-hexane solution (16.56 mL, 1.6 mol/L) was added dropwise
  2. additionafter the completion of the dropwise addition
  3. stirringthe mixture was further stirred at −78° C. for 30 min
  4. stirringthe mixture was stirred at −78° C. for 30 min
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→2/1)

출처 및 근거

ORD 기록
ord-693ae716b3ea4fdd87cc50ad6fde7e42
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834051B2

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