Acetic Acid → HCID 54562909, compound

Reaction equation

[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])([OH:24])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH2:48])=[N-].C(O)(=O)C>ClCCl>[C:1]1([NH:7][C:8](=[O:45])[C@H:9]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:10][C:11](=[O:40])[CH:12]([CH2:21][P:22]([CH2:25][CH2:26][CH2:27][CH2:28][N:29]2[C:37](=[O:38])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]2=[O:39])([O:24][CH3:48])=[O:23])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Procedure

A mixture of dichloromethane (100 mL) and (2-(((4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl)hydroxyphosphinyl)methyl)-4-phenylbutanoyl)-L-leucine N-phenylamide (2.00 g, 3.17 mmol) from Example 1 was warmed to give a clear solution which was then cooled in an ice bath. Diazomethane (0.3M solution in ether) was added until the yellow color persisted and the solution was stired 10 min longer. Glacial acetic acid (0.080 mL, 84 mg, 1.4 mmol) was added to give a colorless solution which was concentrated under vacuum. Methanol (100 mL) was added and the solution was evaporated again and dried under vacuum to give 2.09 g of crude product which was used in the next reaction without further purification.