Hydrochloric Acid → HCID 53692001, 화합물

HRID 53136노트

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HRID 53136 반응식
[Br:1][CH:2]1[CH2:8][CH:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:5]=2[NH:4][C:3]1=[O:20].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C([CH:35](I)[C:36]([NH2:38])=[O:37])(C)(C)C.Cl>O1CCCC1.CS(C)=O>[C:6]([NH:38][C:36](=[O:37])[CH2:35][N:4]1[C:5]2[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:6]=2[CH:7]([CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:8][CH:2]([Br:1])[C:3]1=[O:20])([CH3:15])([CH3:7])[CH3:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18352670HCID 18352670, 화합물HCID 19961863HCID 19961863, 화합물

생성물 1

HCID 53692001HCID 53692001, 화합물수율 34%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

To a 125 mL round-bottomed flask equipped with nitrogen inlet were added 4.7 grams (13.97 mmol) 3-bromo-5-cyclohexyl-8-methyl-2,3,4,5-tetrahydro-1H-(1)benzazepin-2-one and 70 mL dry tetrahydrofuran. The solution was cooled to -78° C., and 16.8 mL (16.76 mmol) of a 1N solution of sodium bistrimethylsilylamide in tetrahydrofuran was added, followed by a solution of 4.04 grams (16.76 mmol) of t-butyl iodoacetamide in 35 mL dry tetrahydrofuran dropwise over 15 minutes. The reaction was stirred for 10 minutes, then warmed, 35 mL dry dimethylsulfoxide added, and the reaction stirred at room temperature for 14 hours. It was then poured into 1N hydrochloric acid, extracted into ethyl acetate, and the organic layer washed with water, saturated aqueous sodium bisulfite solution, brine, dried, and evaporated. The residue was chromatographed on silica gel with hexane/ethyl acetate to afford the two diastereomeric products, the less polar isomer, M.P. 183°-186° C., 2.16 g, 34% yield, and the more polar isomer, M.P. 206.5°-207.5° C., 3.16 g. 50% yield.

후처리

  1. customTo a 125 mL round-bottomed flask equipped with nitrogen inlet
  2. temperaturewarmed
  3. stirringthe reaction stirred at room temperature for 14 hours
  4. extractionextracted into ethyl acetate
  5. washthe organic layer washed with water, saturated aqueous sodium bisulfite solution, brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica gel with hexane/ethyl acetate
  9. customto afford the two diastereomeric products

출처 및 근거

ORD 기록
ord-432f6d3a6d8042a28c0fdebe1a93be44
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618811

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