Dimethylformamide → HCID 11589051, compound

HRID 1785779Notes

Reaction equation

HRID 1785779 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-bc44119fb99945f1a227de3e7c764308
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…