Water → HCID 69562268, compound

HRID 2299007Notes

Reaction equation

HRID 2299007 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[C:18]([C:23]#[N:24])[CH:17]=[CH:16]4)=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.C([O-])([O-])=O.[K+].[K+].Cl[C:32]([O:34][CH3:35])=[O:33].O>O1CCOCC1>[C:23]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([CH:12]=[CH:11][C:7]1[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=1)[CH2:1][N:2]([C:32]([O:34][CH3:35])=[O:33])[CH2:3][CH2:4]3)[CH:22]=[CH:21]2)#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 69561453HCID 69561453, compound

Product 1

HCID 69562268HCID 69562268, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 42J (650 mg, 1.53 mmol) in dioxane (30 mL) at room temperature was treated with 10% K2CO3 (10 mL) and methyl chloroformate (700 mg) and stirred for 16 hours. The mixture was treated with water and extracted with dichloromethane. The combined extracts were washed sequentially with 5% HCl, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with dichloromethane to provide the desired product.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined extracts were washed sequentially with 5% HCl, water, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-2528e4bc03fb4cd9a4ec1d33a26ddcce
Source dataset
uspto-grants-2002_12
Patent number
US06495562B1

Reaction notes

Loading…