Formaldehyde → HCID 86708776, compound

Reaction equation

[CH3:1][CH:2]([CH3:59])[C@H:3]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C:4](=[O:53])[N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[NH:35][C:34]([C@@H:36]6[CH2:40][CH2:39][CH2:38][N:37]6[C:41]([C@H:43]6[C:52]7[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=7)[CH2:46][CH2:45][NH:44]6)=[O:42])=[N:33][CH:32]=5)=[CH:27][CH:26]=4)[CH:21]=3)[CH:16]=2)=[CH:13][N:14]=1.[CH2:60]=O>[Zn].C(O)(=O)C>[CH3:1][CH:2]([CH3:59])[C@H:3]([NH:54][C:55](=[O:58])[O:56][CH3:57])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]1[NH:11][C:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:25]4[CH:30]=[CH:29][C:28]([C:31]5[NH:35][C:34]([C@@H:36]6[CH2:40][CH2:39][CH2:38][N:37]6[C:41]([C@H:43]6[C:52]7[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=7)[CH2:46][CH2:45][N:44]6[CH3:60])=[O:42])=[N:33][CH:32]=5)=[CH:27][CH:26]=4)[CH:21]=3)[CH:16]=2)=[CH:13][N:14]=1)=[O:53]

Participants

Procedure

Methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(6-(4-(2-((S)-1-((R)-1,2,3,4-tetrahydroisoquinoline-1-carbonyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)phenyl)naphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (135 mg, 0.17 mmol), acetic acid (1.7 mL), zinc dust (111 mg, 1.7 mmol), and formaldehyde were all mixed in round bottom flask and stirred at room temperature overnight. The crude mixture was filtered through a celite plug and the filtrate was concentrated down to dryness on rotovap. The residue was then taken up in EtOAc and washed with 10% Na2CO3 and brine and dried over MgSO4. The filtrate was then concentrated down and the residue was purified on reverse phase HPLC. (13 mg, 10%). MS (ESI) m/z 805.77 [M+H]+.