Acetone → HCID 58585190, compound

HRID 2252289Notes

Reaction equation

HRID 2252289 reaction equation
F[C:2](F)(F)[C:3](O)=O.[C:8]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[C:29](=[O:47])[N:30]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)[N:31]=[CH:32][C:33]=3[N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].CC(C)=O.C(I)C.C(N(CC)CC)C>ClCCl>[C:8]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[C:29](=[O:47])[N:30]([C:40]4[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=4)[N:31]=[CH:32][C:33]=3[N:34]3[CH2:39][CH2:38][N:37]([CH2:2][CH3:3])[CH2:36][CH2:35]3)=[CH:25][CH:26]=2)=[CH:17][CH:16]=1)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 8471TriethylamineHCID 69248711HCID 69248711, compound

Product 1

HCID 58585190HCID 58585190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

360 mg (0.44 mmol) of the compound from Example 3 are introduced into 2.0 ml of acetone, and 0.046 ml (0.57 mmol) of ethyl iodide and 0.18 ml (1.32 mmol) of triethylamine are successively added. The mixture is stirred at room temperature overnight before being diluted with dichloromethane, washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated. The crude product is purified by filtration through a silica gel column (mobile phase: dichloromethane/methanol 95:5).

Workup

  1. additionare successively added
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe crude product is purified by filtration through a silica gel column (mobile phase: dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-0b6ec60f67c648b98d936d8c3ff22bf5
Source dataset
uspto-grants-2008_01
Patent number
US07320977B2

Reaction notes

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