Benzyl Bromide → HCID 69231778, compound

HRID 1181053Notes

Reaction equation

HRID 1181053 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([O:15][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:12]=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 69231752HCID 69231752, compound

Product 1

HCID 69231778HCID 69231778, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[5-hydroxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (14.8 mmol) in DMF (100 mL) was added Cs2CO3 (29.6 mmol) and benzyl bromide (16.3 mmol). The reaction mixture was stirred overnight at ambient temperature and diluted with EtOAc (200 mL). The mixture was washed with brine (100 mL) and water (100 mL). The organic layer was dried (Na2SO4) and concentrated to a yellow oil (6.8 g). MS [ES] m/z 428 (M+H)+.

Workup

  1. washThe mixture was washed with brine (100 mL) and water (100 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated to a yellow oil (6.8 g)

Sources & evidence

ORD record
ord-99bc96cf81e64c6c8e731575dd627331
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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