Coupling conditions for the synthesis of bis-O-HETE-N,S-Boc-GSH 12.

Entry	Coupling Agents	Bases	T/°C	t/h	Equiv. TDG	Yield/%	Purity/% (H NMR)
1	EDC	—	0 °C – >r.t.	24	13	19	95
2	EDC	—	0 °C – >r.t.	22	26	13	50
3	EDC/HOBt	—	0 °C – >r.t.	22	26	50	70
4	EDC/HOBt	DMAP	0 °C – >r.t.	22	26	55	70
5	EDC/HOBt	TEA	0 °C – >r.t.	22	26	40	57
6	EDC/HOBt	DMAP/TEA	0 °C – >r.t.	22	26	40	59
7	EDC	DMAP	0 °C – >r.t.	22	26	34	54
8	EDC	DMAP/TEA	0 °C – >r.t.	22	26	24	63
9	EDC	TEA	0 °C – >r.t.	22	26	7	38
10	EDC/HOBta	DMAP	0 °C – >r.t.	22	26	69	68

^aReaction conducted under inert atmosphere.