Dimethylformamide → HCID 11589051, compound

HRID 2085700Notes

Reaction equation

HRID 2085700 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1.[C:24](Cl)(=[O:28])[C:25](Cl)=O.C[N:31]([CH:33]=O)C.Cl[CH2:36]Cl>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]([N:31]2[CH2:25][CH2:24][O:28][CH2:36][CH2:33]2)=[O:13])[CH:6]=[CH:5][C:4]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 11652570HCID 11652570, compound

Product 1

HCID 11589051HCID 11589051, compound

Procedure

A solution of Example 122L (500 mg, 1.59 mmol) in dichloromethane (5 mL) was treated with 2M oxalyl chloride in dichloromethane (1 mL) and a drop of DMF, stirred for 1 hour, concentrated under vacuum, and dissolved in dichloromethane (5 mL). The mixture was treated with morpholine (0.5 mL) and the resulted slurry was filtered through silica gel (10 g). The silica gel was rinsed with ethyl acetate and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 384 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutiondissolved in dichloromethane (5 mL)
  3. additionThe mixture was treated with morpholine (0.5 mL)
  4. filtrationthe resulted slurry was filtered through silica gel (10 g)
  5. washThe silica gel was rinsed with ethyl acetate
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-723342d345e84e75a1b9a8361f63c4fe
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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