Water → HCID 57535889, compound

HRID 1455791Notes

Reaction equation

HRID 1455791 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([CH2:33][OH:34])([CH2:30][C:31]#[CH:32])[C:26]([O:28][CH3:29])=[O:27])=[C:18]([Cl:35])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[CH2:43](Cl)[O:44][CH3:45].O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][C:25]([CH2:33][O:34][CH2:43][O:44][CH3:45])([CH2:30][C:31]#[CH:32])[C:26]([O:28][CH3:29])=[O:27])=[C:18]([Cl:35])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 7912DiisopropylamineHCID 23078193HCID 23078193, compound

Product 1

HCID 57535889HCID 57535889, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of Example 212 (1.12 g) was dissolved in acetonitrile (30 mL). To this solution, diisopropylamine (0.58 mL) and MOMCl (0.25 mL) were added while the solution was stirred and chilled in an ice bath. The mixture was stirred overnight. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous magnesium sulfate. The solvent was concentrated and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=5:1) to give the desired product as a colorless oil (1.12 g).

Workup

  1. temperaturechilled in an ice bath
  2. stirringThe mixture was stirred overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated
  7. customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e358e0bdc7c64568b48049b875c4ab0f
Source dataset
uspto-grants-2009_01
Patent number
US07482491B2

Reaction notes

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