Diisopropylethylamine → HCID 52945681, compound
Reaction equation
[CH3:1]CN(C(C)C)C(C)C.[CH3:10][CH2:11][C@H:12]([C@H:14]([NH:59][C:60]([C@@H:62]1[N:67]([CH3:68])[CH2:66][CH2:65][CH2:64][CH2:63]1)=[O:61])[C:15]([N:17]([C@@H:26]([CH:56]([CH3:58])[CH3:57])[CH2:27][C@@H:28]([O:52][C:53]([CH3:55])=[O:54])[C:29]1[S:33][CH:32]=[C:31]([C:34]([NH:36][C@H:37]([CH2:46][C@@H:47]([C:49]([OH:51])=[O:50])[CH3:48])[CH2:38][C:39]2[CH:40]=[CH:41][C:42](O)=[CH:43][CH:44]=2)=[O:35])[N:30]=1)[CH2:18][O:19][C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[O:16])[CH3:13]>CN(C=O)C>[CH3:10][CH2:11][C@@H:12]([C@H:14]([NH:59][C:60]([C@@H:62]1[N:67]([CH3:68])[CH2:66][CH2:65][CH2:64][CH2:63]1)=[O:61])[C:15]([N:17]([C@@H:26]([CH:56]([CH3:58])[CH3:57])[CH2:27][C@@H:28]([O:52][C:53]([CH3:55])=[O:54])[C:29]1[S:33][CH:32]=[C:31]([C:34]([NH:36][C@H:37]([CH2:46][C@@H:47]([C:49]([OH:51])=[O:50])[CH3:48])[CH2:38][C:39]2[CH:44]=[CH:43][C:42]([CH3:1])=[CH:41][CH:40]=2)=[O:35])[N:30]=1)[CH2:18][O:19][C:20]([CH2:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[O:16])[CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of pyridine dithioethylamine hydrochloric salt (15.8 mg, 0.071 mmole) in anhydrous DMF (1.5 mL) was added DIEA (25 μL, 0.142 mmole) followed by a solution of tubulysin A (40 mg, 0.047 mmole) in anhydrous DMF (0.5 mL). The reaction mixture was stirred under argon at room temperature for 2 h. The mixture was then evaporated under vacuum. The crude product was purified by silica gel column chromatography (CH2Cl2/MeOH, 15/1) to afford white solid (54 mg) in quantitative yield.
Workup
- customThe mixture was then evaporated under vacuum
- customThe crude product was purified by silica gel column chromatography (CH2Cl2/MeOH, 15/1)
Sources & evidence
- ORD record
- ord-0f4d206f38da45d897309f0fcb96921e
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497365B2
Reaction notes
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