Dimethylformamide → HCID 58617404, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:41](=[O:42])[C:40]3[CH:43]=[CH:44][CH:45]=[N:46][C:39]=3[N:38]=[C:37]2[C@H:47]([NH:49][CH2:50][CH2:51][C:52](=[O:54])[CH3:53])[CH3:48])=[CH:32][CH:31]=1)[CH3:28].C(N(CC)CC)C>ClCCl>[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:41](=[O:42])[C:40]3[CH:43]=[CH:44][CH:45]=[N:46][C:39]=3[N:38]=[C:37]2[C@H:47]([N:49]([CH2:50][CH2:51][C:52](=[O:54])[CH3:53])[C:9](=[O:11])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:12]([F:15])([F:14])[F:13])[CH:4]=2)[CH3:48])=[CH:32][CH:31]=1)[CH3:28]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
4-fluoro-3-trifluoromethylphenylacetic acid (707 mg, 3.18 mmol) was dissolved in dichloromethane and cooled to 0° C. Oxalyl chloride (278 μL, 3.18 mmol) was added, then after 5 min, dimethylformamide (24.7 μL, 0.32 mmol) was added. The reaction stirred at 0° C. for 30 min and room temperature for 1 h. The solution was added slowly to a mixture of E2 (713 mg, 1.87 mmol) and triethylamine (784 μL, 5.62 mmol) in dichloromethane at −78° C. The reaction stirred for 30 min, then was washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, concentrated in vacuo. Purified by column (2% to 10% methanol in dichloromethane), to yield 859 mg of E3.
Workup
- stirringThe reaction stirred for 30 min
- washwas washed with saturated aqueous sodium bicarbonate and brine
- dry with materialIt was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurified by column (2% to 10% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-53193c3250cc4faa9ec990ff509de6f8
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375102B2
Reaction notes
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