. 2022 Jun 22;7(26):22915–22929. doi: 10.1021/acsomega.2c02913

Table 3. Efforts to Optimize Amide Formation to Prepare Compound 37.

entry	coupling agent	additive	base	yield (%)^a
1	EDC	none	none	19^b
2	EDC^d	HOBt	none	19^b–31^c
3	COMU	none	i-Pr₂NEt	76^b–51^c
4	HBTU	none	i-Pr₂NEt	29^b
5	DCC	none	none	29^b
6	DCC	oxyma	none	75^b–60^c
7	DCC	HOBt	none	57^c

Isolated yield after chromatography.

Small scale (≤0.1 mmol).

Large scale (≥1 mmol).

CH₂Cl₂ was used.