Hydrochloric Acid → HCID 53692001, compound

HRID 53136Notes

Reaction equation

HRID 53136 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18352670HCID 18352670, compoundHCID 19961863HCID 19961863, compound

Product 1

HCID 53692001HCID 53692001, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-432f6d3a6d8042a28c0fdebe1a93be44
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Reaction notes

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