Triethylamine → HCID 18402470, compound

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) δC 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.

1. customExcess of oxalyl chloride was removed in vacuo
2. additionwas added
3. stirringThe reaction mixture was stirred at RT overnight
4. customThe reaction was then quenched with 1 M aqueous HCl (100 mL)
5. customdried
6. concentrationconcentrated in vacuo

ORD record

ord-0d73173f106a4ebf8195700e2328892e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09168317B2