Iodoethane → HCID 9933783, compound

HRID 1700277Notes

Reaction equation

HRID 1700277 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:11][C:12]1[CH:35]=[CH:34][C:15]([CH2:16][C@@:17]2(CC)[NH:21][C:20](=[O:22])[N:19]([C:23]3[CH:28]=[C:27]([Cl:29])[N:26]=[C:25]([Cl:30])[CH:24]=3)[C:18]2=[O:31])=[CH:14][CH:13]=1.I[CH2:37][CH3:38].[CH2:39]1COCC1>C1(C)C=CC=CC=1>[Br:11][C:12]1[CH:35]=[CH:34][C:15]([CH2:16][C@@:17]2([CH3:39])[N:21]([CH2:37][CH3:38])[C:20](=[O:22])[N:19]([C:23]3[CH:28]=[C:27]([Cl:29])[N:26]=[C:25]([Cl:30])[CH:24]=3)[C:18]2=[O:31])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 3251421Potassium bis(trimethylsilyl)amideHCID 22949182HCID 22949182, compound

Product 1

HCID 9933783HCID 9933783, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.12 mL (0.559 mmol) of 0.5 M potassium bis(trimethylsilyl)amide in toluene was added to a solution of 0.16 g (0.373 mmol) of the product of Example 1 and 0.149 mL (1.86 mmol) iodoethane in 3.5 mL dry THF+0.13 mL (0.746 mmol) HMPA. The reaction was refluxed overnight, quenched with aqueous NH4Cl, extracted 4× with ether, washed 3× with H2O, dried and concentrated in vacuo to an oil. Purification on Analtech 2 mm prep plates, developed in 15% acetone-petroleum ether, afforded 143 mg (84%) of sticky glassy resin. (−)-Electrospray mass spec (M+35 490) was consistent with the structure.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customquenched with aqueous NH4Cl
  3. extractionextracted 4× with ether
  4. washwashed 3× with H2O
  5. customdried
  6. concentrationconcentrated in vacuo to an oil
  7. customPurification on Analtech 2 mm prep plates

Sources & evidence

ORD record
ord-a0f093ea1a35439ab37dee5ea58825dd
Source dataset
uspto-grants-2002_02
Patent number
US06350763B1

Reaction notes

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