Water → HCID 67473782, compound

HRID 403282Notes

Reaction equation

HRID 403282 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>CN(C=O)C.CCOC(C)=O>[C:1]([N:9]1[CH2:13][CH2:12][C@H:11]([N:14]([CH3:24])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53256055HCID 53256055, compound

Product 1

HCID 67473782HCID 67473782, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 4b (0.15 g, 0.517 mmol) in DMF (2 mL) was added NaH (60% in mineral, 31 mg, 0.775 mmol) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 30 min and then MeI (0.065 mL, 1.034 mmol) was added. The reaction was allowed to warm to room temperature with continuous stirring for 2 h. To the reaction mixture was added water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 35% EtOAc/hexanes) gave compound 4c (0.12 g). MS m/z (M-Boc+) 204.2.

Workup

  1. temperatureto warm to room temperature
  2. stirringwith continuous stirring for 2 h
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by flash column chromatography (silica gel, 35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7e765c8f340a4842b2000cc79fe343df
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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