Water → HCID 67429355, compound

HRID 1662668Notes

Reaction equation

HRID 1662668 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@@H:11]([CH3:17])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:18])[N:10]([CH2:22][CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@@H:11]([CH3:17])[C:12]([N:14]([CH3:15])[CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 69348250Phenylmethyl N-[(1S)-2-(dimethylamino)-1-methyl-2-oxoethyl]carbamate

Product 1

HCID 67429355HCID 67429355, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere, to a solution of 2.78 g of the compound obtained in Step 79-1 in DMF (30 ml) was added 0.66 g of NaH under ice cooling. The solution was stirred at room temperature for one hour, then, 3.58 g of [(2-bromoethoxy)methyl]benzene was added. The solution was stirred at room temperature for two hours, then, water was added, and the resulting mixture was extracted with EtOAc. The organic layers were combined, washed with saturated brine and dried over MgSO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=2/3; v/v) to obtain 3.22 g of the title compound (pale yellow oil).

Workup

  1. stirringThe solution was stirred at room temperature for two hours
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washwashed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe drying agent was separated by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=2/3; v/v)

Sources & evidence

ORD record
ord-063c68cc90404988aade66e1129c7a49
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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