Water → HCID 12021102, compound

HRID 1016306Notes

Reaction equation

HRID 1016306 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6]4=[C:7]([C:18](=[O:28])[C:19]([CH2:21][C:22]5[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=5)=[CH:20][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([OH:17])[CH:10]=3.Br[CH2:30][CH2:31][CH2:32][OH:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6]4=[C:7]([C:18](=[O:28])[C:19]([CH2:21][C:22]5[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=5)=[CH:20][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:17][CH2:30][CH2:31][CH2:32][OH:33])[CH:10]=3

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 12021101HCID 12021101, compound

Product 1

HCID 12021102HCID 12021102, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (47 mg) obtained in Example 33 was suspended in DMF (2 mL) and to the suspension was added 3-bromopropanol (11 μL) and potassium carbonate(19 mg) The mixture was stirred at room temperature overnight. After addition of water, the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylene chloride:methanol=100:0˜10:1) to obtain the title compound (27 mg; 51%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: methylene chloride:methanol=100:0˜10:1)

Sources & evidence

ORD record
ord-1e2f0b2fc2e74fbfae62530e21b1dd1e
Source dataset
uspto-grants-2002_11
Patent number
US06476021B1

Reaction notes

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