Water → HCID 67186122, compound

HRID 1441972Notes

Reaction equation

HRID 1441972 reaction equation
I[CH3:2].[H-].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([C:23]([F:26])=[CH:24][CH:25]=1)[CH2:9][C@@H:10]([C:19]([O:21][CH3:22])=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O>O1CCCC1.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([C:23]([F:26])=[CH:24][CH:25]=1)[CH2:9][C@@H:10]([C:19]([O:21][CH3:22])=[O:20])[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67188462HCID 67188462, compound

Product 1

HCID 67186122HCID 67186122, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

49.8 g (350.86 mmol) of iodomethane and 2.28 g (57.01 mmol) of sodium hydride are added to a solution of 16.5 g (43.86 mmol) of methyl 3-bromo-N-(tert-butoxycarbonyl)-6-fluoro-L-phenylalaninate (Example 5O) in 220 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred at RT overnight. 1000 ml of water and 1000 ml of ethyl acetate are added to the mixture. The organic phase is washed successively with water and a saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 3:1).

Workup

  1. washThe organic phase is washed successively with water
  2. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by column chromatography on silica gel (mobile phase: cyclohexane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-3bc0022957404f2e9f3c5428cf05ac7a
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

Loading…