Methanol → HCID 19782203, compound

HRID 1612978Notes

Reaction equation

HRID 1612978 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]3[CH2:15][CH:14]([C:16]([OH:18])=[O:17])[CH2:13][C:11]3=[CH:12][C:4]=2[O:3]1.CO.[CH:22]1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:19])[CH2:7][C:6](=[O:8])[C:5]2[CH:9]=[C:10]3[CH2:15][CH:14]([C:16]([O:18][CH3:22])=[O:17])[CH2:13][C:11]3=[CH:12][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 19782199HCID 19782199, compound

Product 1

HCID 19782203HCID 19782203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

4.98 g (19.2 mmol) of the compound from Example 15 are dissolved in 38 ml of CH2Cl2 and 19 ml of absolute MeOH and 4.35 g (21.1 mmol) of dicyclohexylcarbodiimide and 20 ml of dimethylaminopyridine are added at 0° C. The mixture is allowed to come to room temperature and is stirred at 20° C. for 2 h. Precipitated dicyclohexylurea is filtered off and washed well with CH2Cl2, and the combined CH2Cl2 phases are washed twice with 1N NaOH solution, once with 1N hydrochloric acid and once with NaCl solution. After drying over Na2SO4, the solution is evaporated and the residue is flash chromatographed on silica gel (eluent: methylene chloride)

Workup

  1. customto come to room temperature
  2. filtrationPrecipitated dicyclohexylurea is filtered off
  3. washwashed well with CH2Cl2
  4. washthe combined CH2Cl2 phases are washed twice with 1N NaOH solution, once with 1N hydrochloric acid and once with NaCl solution
  5. dry with materialAfter drying over Na2SO4
  6. customthe solution is evaporated
  7. customchromatographed on silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-abebc7f8b7e9433bb70754f4843b6c7d
Source dataset
uspto-grants-1993_03
Patent number
US05191092

Reaction notes

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