Water → HCID 86663480, compound

HRID 446615Notes

Reaction equation

HRID 446615 reaction equation
[NH2:1][C:2]1[C:14]([Cl:15])=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([O:16][CH3:17])[CH:3]=1.[H-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].O>CN(C)C=O.C(OCC)(=O)C>[Cl:15][C:14]1[C:2]([NH:1][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:3][C:4]([O:16][CH3:17])=[C:5]([CH:13]=1)[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 54929897HCID 54929897, compound

Product 1

HCID 86663480HCID 86663480, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (480 mg, 1.86 mmol) obtained in Example 99a was dissolved in N,N-dimethylformamide (6 mL), 55% sodium hydride (89 mg, 2.79 mmol) was added under ice cooling, and the mixture was stirred at the same temperature under a nitrogen atmosphere for 20 minutes. Subsequently, ethyl 6-bromohexanoate (623 mg, 2.79 mmol) was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate, 1:3, v/v) to give the title compound (338 mg; yield, 45%) as a pale orange color oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customto separate the layers
  3. customThe resulting organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-0aff4429e5d44e42b18f58963590ccdf
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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