Dimethylformamide → HCID 15341811, compound

HRID 1756202Notes

Reaction equation

HRID 1756202 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH:12]=[CH2:13])=[C:9]([OH:14])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].I[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:33]=[CH:32][C:23]2[CH2:24][CH2:25][CH:26]([C:28]([O:30][CH3:31])=[O:29])[O:27][C:22]=2[C:21]=1[CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[NH2:6][C:4]([C:3]1[CH:7]=[CH:8][C:9]([O:14][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]3[CH2:24][CH2:25][CH:26]([C:28]([O:30][CH3:31])=[O:29])[O:27][C:22]=3[C:21]=2[CH2:34][CH2:35][CH3:36])=[C:10]([CH2:11][CH:12]=[CH2:13])[C:2]=1[OH:1])=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 14722828HCID 14722828, compoundHCID 15341803HCID 15341803, compound

Product 1

HCID 15341811HCID 15341811, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 20 (550 mg, 2.89 mmol), the compound of Example 23 (1.21 g, 2.89 mmol), and potassium carbonate (800 mg, 5.78 mmol) were added to about 25 to 30 ml of DMF. The reaction mixture as stirred at room temperature for 12 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude material was chromatographed on silica gel with 30% ethyl acetate/hexane as eluant. The fractions containing the product were collected and the solvent was removed under vacuum to give the product as a white solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude material was chromatographed on silica gel with 30% ethyl acetate/hexane as eluant
  5. additionThe fractions containing the product
  6. customwere collected
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8dda26aaa5664e84bdc919ddda84a077
Source dataset
uspto-grants-1995_08
Patent number
US05439937

Reaction notes

Loading…