Triethylamine → HCID 178523565, compound

Reaction equation

N1C=CC=CC=1S[S:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH-:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24].C(S)[C@@H](O)[C@H](O)CS.CCN(CC)CC>CO>[SH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH-:18][CH:17]=[CH:16][CH:15]=1)=[O:13].[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

Procedure

To a solution of 12 (113 mg, 0.28 mmol) dissolved in 6 mL of MeOH was added DTT (438 mg, 2.8 mmol) and Et3N (79 mL, 0.57 mmol). The solution was stirred at room temperature for 18 h, followed by evaporation of the solvent. The residue was dissolved in 15 mL of EtOAc and rinsed with H2O (8×15 mL) to remove excess DTT. After drying over MgSO4 and concentrating, the residue was purified by flash chromatography (hexanes/EtOAc, 1:1, v/v) to afford 46 mg (57%) of 13. 1H NMR 400 MHz (CDCl3) d 6.16 (br s, 1 H), 4.66 (t, J=1.8 Hz, 2 H), 4.33 (t, J=1.8 Hz, 2 H), 4.19 (s, 5 H), 3.53 (q, J=6.4 Hz, 2 H), 2.75 (m, 2 H).