Water → HCID 71277437, compound

HRID 1429369Notes

Reaction equation

HRID 1429369 reaction equation
[C:1]([O:5][CH2:6][C@@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:24][C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28].O>CN(C=O)C>[CH2:13]([O:12][C:11]([NH:10][C@H:7]([CH2:6][O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:8][O:9][CH2:24][C:25]1[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 71277436HCID 71277436, compound

Product 1

HCID 71277437HCID 71277437, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 14b (562 mg, 2.0 mmol) in DMF (10 mL) at 0° C. was added NaH (200 mg, 5.0 mmol). The reaction was stirred for 30 min and to it was added methyl 2-(bromomethyl)benzoate (366 mg, 1.6 mmol). The reaction mixture was stirred for 3 h, poured into H2O and extracted with EA (10 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give compound 14c (275 mg, 40% yield) as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. extractionextracted with EA (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by Prep-TLC

Sources & evidence

ORD record
ord-b6c87f095cd44dd7bdeac8fab46731f5
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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