Dimethylformamide → HCID 15896094, compound

HRID 347655Notes

Reaction equation

HRID 347655 reaction equation
[C:1]([CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7])([OH:3])=[O:2].[CH3:30]N(C=O)C.C(Cl)(=O)C(Cl)=O>ClCCl>[CH3:30][O:2][C:1](=[O:3])[CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 15896092HCID 15896092, compound

Product 1

HCID 15896094HCID 15896094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxylic acid from Example 33 (0.080 g, 0.20 mmol) under a nitrogen atmosphere in dichloromethane (25 ml) at 0° C. were added DMF (20 □l) and oxalyl chloride (31 mg, 0.24 mmol). The mixture was stirred at 0° C. to room temperature for 2 h and then concentrated in vacuo. The residue was dissolved in methanol (4 ml) and dichloromethane (16 ml) and the mixture stirred at room temperature for 16 h. The mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4) to give a white solid; yield 0.049 g (60%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol (4 ml)
  3. stirringdichloromethane (16 ml) and the mixture stirred at room temperature for 16 h
  4. washThe mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4)
  8. customto give a white solid

Sources & evidence

ORD record
ord-851df4d5ef5349ad8f26bc38e78d7acf
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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