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Ammonium Chloride → (3S,4R)-4-[(1-Ethyl-5-methylpyrazol-3-yl)carbonylmethyl]-3-[(R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one

HRID 1825348
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HRID 1825348 반응식
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH3:11])[N:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(O[C@H:26]1[NH:29][C:28](=[O:30])[C@@H:27]1[C@H:31]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH3:32])(=O)C.[Cl-].[NH4+]>O.C(OCC)(=O)C.C1COCC1>[CH2:10]([N:6]1[C:7]([CH3:9])=[CH:8][C:4]([C:1]([CH2:2][C@H:26]2[NH:29][C:28](=[O:30])[C@@H:27]2[C@H:31]([O:33][Si:34]([C:37]([CH3:38])([CH3:40])[CH3:39])([CH3:36])[CH3:35])[CH3:32])=[O:3])=[N:5]1)[CH3:11]
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참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium hexamethyldisilazaneHCID 10935078AzetidonHCID 221453691-(1-Ethyl-5-methyl-1H-pyrazol-3-yl)ethanone

생성물 1

HCID 10691156(3S,4R)-4-[(1-Ethyl-5-methylpyrazol-3-yl)carbonylmethyl]-3-[(R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one수율 41.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

3-Acetyl-1-ethyl-5-methylpyrazole (3.51 g) in dry tetrahydroturan (THF) (150 ml) under an argon atmosphere was cooled in an acetone/solid carbon dioxide bath and then treated with a 1M solution of lithium bis(trimethylsilyl)amide (50 ml). The mixture was stirred for 45 minutes and then (3R,4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]azetidinone (6.6 g) was added as a solid under a blanket of argon. The mixture was stirred in the cold for 3.5 h. Saturated aqueous ammonium chloride was then added, followed by ethyl acetate, and the mixture was allowed to warm to room temperature. A little water was added and the layers were separated and the aqueous layer was re-extracted with ethyl acetate. The combined ethyl acetate extracts were washed with saturated brine, dried and evaporated. Chromatography on silica gel, eluting with ethyl acetate/hexane mixtures gave the title compound (3.65 g), υmax (CH2Cl2) 3411, 1761, 1678, 1376, 1151, and 838 cm−1; δ(CDCl3) 0.064 (6H, s), 0.86 (9H, s), 1.20 (3H,d, J 6.3 Hz), 1.44 (3H, t, J 7.3 Hz), 2.31 (3H, s), 2.89 (1H, dd, J 1.8 & 4.9 Hz), 3.15 (1H, dd, J 10.0 & 17.1 Hz), 3.50 (1H, dd, J3.5 & 17.0 Hz), 4.06-4.25 (4H, m), 6.11 (1H, s), 6.53 (1H, s), (Found m/z 379.2296. C19H33N3O3Si requires m/z 379.2291),

후처리

  1. stirringThe mixture was stirred in the cold for 3.5 h
  2. customthe layers were separated
  3. extractionthe aqueous layer was re-extracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with saturated brine
  5. customdried
  6. customevaporated
  7. washChromatography on silica gel, eluting with ethyl acetate/hexane mixtures

출처 및 근거

ORD 기록
ord-c85304adfcbb41c883289d75930e75e9
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07045619B2

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