Dimethylformamide → HCID 15341789, compound

HRID 1033620Notes

Reaction equation

HRID 1033620 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]([OH:15])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].I[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:36]=[CH:35][C:24]2[CH2:25][CH2:26][CH:27]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[O:28][C:23]=2[C:22]=1[CH2:37][CH2:38][CH3:39].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]([CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5])[O:15][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:36]=[CH:35][C:24]2[CH2:25][CH2:26][CH:27]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[O:28][C:23]=2[C:22]=1[CH2:37][CH2:38][CH3:39]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15341787HCID 15341787, compoundHCID 15341788HCID 15341788, compound

Product 1

HCID 15341789HCID 15341789, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 6 (465 mg), the compound of Example 3 (1 g) and potassium carbonate (312 mg) were added to 5.0 ml of dimethylformamide (DMF), and the reaction mixture was stirred at room temperature for about 2 days. Water (20 ml) was added and the reaction mixture was extracted three times with ethyl acetate and the combined extracts washed twice with water, dried and filtered. Solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel with 20/80 ethyl acetate/hexane gave the product as a white solid.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. washthe combined extracts washed twice with water
  3. customdried
  4. filtrationfiltered
  5. customSolvent was removed under vacuum
  6. customto give an oil

Sources & evidence

ORD record
ord-90929e81f3714b67ab433a2d2c621f43
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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