Triethylamine → HCID 18402470, compound
Reaction equation
[CH2:1]([O:8][CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[F:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]([NH:30][C:29]1[CH:31]=[CH:32][CH:33]=[C:27]([F:26])[CH:28]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
To a solution of benzyloxyacetic acid (4.65 g, 28 mmol, 4.0 mL) in DCM (52 mL) was added oxalyl chloride (7.7 g, 61 mmol, 5.3 mL) and a drop of DMF. The reaction mixture was stirred at room temperature for 4 h. Excess of oxalyl chloride was removed in vacuo and the crude acyl chloride was diluted into DCM (100 mL) and triethylamine (5.3 mL, 41.6 mmol, 4.2 g) was added followed by 3-fluoroaniline (3.5 g, 32 mmol, 3.0 mL). The reaction mixture was stirred at RT overnight. The reaction was then quenched with 1 M aqueous HCl (100 mL), dried and concentrated in vacuo to afford 7.10 g (95%) of 2-benzyloxy-N-(3-fluoro-phenyl)-acetamide (39) as a yellow oil which was used in the next step without purification. The structure was confirmed by 13C NMR (75 MHz, CDCl3) be 69.2, 73.5, 106.9, 107.2, 111.0 (d, JCF=24 Hz), 114.9 (d, JCF=3 Hz), 127.8, 128.2, 128.5, 129.7 (d, JCF=9 Hz), 136.2, and 167.6.
Workup
- customExcess of oxalyl chloride was removed in vacuo
- additionwas added
- stirringThe reaction mixture was stirred at RT overnight
- customThe reaction was then quenched with 1 M aqueous HCl (100 mL)
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-619a95a8036849978947f2bd5ab94abb
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08790619B2
Reaction notes
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