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

HRID 1603661
ノート
印刷プレビュー

反応式

HRID 1603661 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 5360545SodiumHCID 135978376-Phenylhexanoyl chloride2 回HCID 19605267(4-Benzylthio-2-oxoazetidin-1-yl)acetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
4 回

反応条件

温度
-10 °C

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-c9dcc51d6f964276af2da492dc1d66de
出典データセット
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05990102

反応ノート

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