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Sodium hydride → N-(6-Phenylhexanoyl)-(4-benzylthio-2-oxoazetidin-yl)acetamide

HRID 1603661
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HRID 1603661 반응식
[CH2:1]([S:8][CH:9]1[N:12]([CH2:13][C:14]([NH2:16])=[O:15])[C:11](=[O:17])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+]>C1COCC1>[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH:16][C:14](=[O:15])[CH2:13][N:12]2[CH:9]([S:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:10][C:11]2=[O:17])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
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참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 5360545SodiumHCID 135978376-Phenylhexanoyl chloride2회HCID 19605267(4-Benzylthio-2-oxoazetidin-1-yl)acetamide

생성물 1

HCID 19605348N-(6-Phenylhexanoyl)-(4-benzylthio-2-oxoazetidin-yl)acetamide수율 21%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
4회

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온도
-10 °C

실험 절차

A solution of (4-benzylthio-2-oxoazetidin-1-yl)acetamide (0.63 g, 2.52 mmol) in dry THF (15 ml) was added to a suspension of sodium hyride (60% in oil, 0.10 g, 2.5 mmol) in dry THF at -10° C. under a nitrogen atmosphere. The reaction was stirred at -10° C. for 10 minutes and was then treated with a solution of 6-phenylhexanoyl chloride (0.58 g, 2.75 mmol) in dry THF (5 ml) dropwise over 2 minutes maintaining the temperature at -10° C. The cooling bath was removed an after stirring for 60 minutes the reaction was treated with sodium hydride (50 mg, 1.25 mmol) and 6-phenylhexanoyl chloride (0.29 g, 1.38 mmol) in dry THF (2 ml). The reaction was stirred for 60 minutes, poured into ice/brine (100 ml), extracted with ethyl acetate (2×50 ml). The organic extracts were combined, washed with aq. sat. NaHCO3 solution, brine, dried (MgSO4) and evaporated under reduced pressure to an orange oil. Purification by repeated column chromatography eluted with hexane:ethyl acetate (3:1 to 1:1) gave the product as a colourless oil (0.22 g, 21% yield, contains 10% 6-phenylhexanoic acid) 1H nmr δ (CDCl3) 1.3-1.7 (6H, m, 3×CH2), 2.44 (2H, t, J=7.4 Hz, NHCOCH2), 2.62 (2H, t, J=7.6 Hz, PhCH2), 2.96, 3.02 (1H, dd, J=2.4, 15.3 Hz, H3), 3.39, 3.45 (1H, dd, J=5.1, 15.3 Hz, H3), 3.61, 4.32 (each 1H, d, J=18.8 Hz, NCH2CO), 3.76 (2H, m, SCH2), 4.9 (1H, m, H4), 7.1-7.3 (10H, m, 2×Ph--H), 8.17 (1H, m, NH)

후처리

  1. temperaturemaintaining the temperature at -10° C
  2. customThe cooling bath was removed
  3. stirringan after stirring for 60 minutes the reaction
  4. stirringThe reaction was stirred for 60 minutes
  5. extractionextracted with ethyl acetate (2×50 ml)
  6. washwashed with aq. sat. NaHCO3 solution, brine
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure to an orange oil
  9. customPurification
  10. washeluted with hexane:ethyl acetate (3:1 to 1:1)

출처 및 근거

ORD 기록
ord-c9dcc51d6f964276af2da492dc1d66de
출처 데이터셋
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05990102

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