HCID 86605971, compound → HCID 69520108, compound

HRID 851961Notes

Reaction equation

HRID 851961 reaction equation
[CH3:1][CH2:2][Mg+].[Br-].Cl[C:6]1[N:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:19][C@@H:18]3[CH2:20][C@H:15]2[CH2:16][N:17]3[C@H:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH3:32])=[C:25]([CH3:33])[C:24]=2[CH3:34])[CH3:22])=[O:13])=[CH:8][CH:7]=1>C1COCC1.CN1CCCC1=O.[Cl-].[Na+].O>[CH2:1]([C:6]1[N:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:19][C@@H:18]3[CH2:20][C@H:15]2[CH2:16][N:17]3[C@H:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH3:32])=[C:25]([CH3:33])[C:24]=2[CH3:34])[CH3:22])=[O:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 2

HCID 86605971HCID 86605971, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 69520108HCID 69520108, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Fe(acac)3 (5 mg) followed by EtMgBr (0.73 mL, 1N in THF) is added to a solution of the amide obtained in Example 4 (129 mg) in 3 mL of THF and 0.3 mL of N-methylpyrrolidinone at room temperature under N2. The dark purple reaction mixture is stirred at room temperature for 50 min and then diluted with brine and extracted 3 times with EtOAc (10 mL). The combined extracts are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by preparative thin layer chromatography, developing 2 times with 25-1 CHCl3-MeOH (25-1) to afford the desired product. LC/MS: 422 (M+1).

Workup

  1. extractionextracted 3 times with EtOAc (10 mL)
  2. dry with materialThe combined extracts are dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-321e1553291749a187f121f8ffdbd5c0
Source dataset
uspto-grants-2007_08
Patent number
US07253168B2

Reaction notes

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