Dimethylformamide → HCID 136375556, compound

HRID 2259601Notes

Reaction equation

HRID 2259601 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([OH:11])[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]([OH:18])[N:6]=1)[CH2:2][CH2:3][CH3:4].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:30][O:31][C:32]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Br)=[CH:36][CH:35]=1)=[O:33]>O>[CH2:1]([C:5]1[N:10]([CH2:38][C:37]2[CH:36]=[CH:35][C:34]([C:32]([O:31][CH3:30])=[O:33])=[CH:41][CH:40]=2)[C:9](=[O:11])[C:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]([OH:18])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178441872HCID 178441872, compound

Product 1

HCID 136375556HCID 136375556, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 mg of the product of Step D of Example 1 were introduced into 4 ml of dimethylformamide, 108 mg of potassium carbonate and 106 mg of [4-(methoxycarbonyl)-benzyl]-bromide. The mixture was stirred at ambient temperature for 6 hours, followed by pouring into water, extracting 3 times with ethyl acetate, washing with a saturated solution of sodium chloride and evaporating to dryness under reduced pressure. After chromatography on silica (eluant: methylene chloride-ethyl acetate: 6-4), 55 mg of the expected product melting at 170° C. were obtained.

Workup

  1. extractionextracting 3 times with ethyl acetate
  2. washwashing with a saturated solution of sodium chloride
  3. customevaporating to dryness under reduced pressure

Sources & evidence

ORD record
ord-d01b1fa8900040d58c729dae838ff37e
Source dataset
uspto-grants-1995_12
Patent number
US05474996

Reaction notes

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