Ethyl chloroformate → HCID 71073409, compound

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:50])[C:25]([C:27]4([NH:31][C:32](=[O:49])[CH:33]([NH:41][C:42]([O:44][C:45](C)(C)[CH3:46])=[O:43])[CH2:34][C:35]5([F:40])[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH2:30][CH2:29][CH2:28]4)=[O:26])=[N:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O>Cl.O1CCOCC1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:50])[CH:25]([C:27]4([NH:31][C:32](=[O:49])[CH:33]([NH:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:34][C:35]5([F:40])[CH2:39][CH2:38][CH2:37][CH2:36]5)[CH2:28][CH2:29][CH2:30]4)[OH:26])=[N:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

Procedure

Compound 57-e (0.079 mmol) was dissolved in 4M HCl in dioxane (3 mL) and then stirred for 4 hrs at room temperature. The solution was concentrated under vacuum and the crude portioned between aq. K2CO3 (0.5 M) and DCM. The aqueous phase was extracted with EtOAc, the combined organic layers were dried over anh. Na2SO4 and concentrated under vacuum. The resulting amine was dissolved in dry DCM (3 mL) and an excess of solid NaHCO3 was added, followed by addition of ethyl chloroformate (7.5 μL, 0.079 mmol). The reaction was stirred for 2 hrs, then filtered and concentrated. (MS m/z 662.05 (M+H).+ The crude compound was used in next step without further purification.