Triethylamine → HCID 68775765, compound
Reaction equation
ClC(OCC(C)C)=O.C(N(CC)CC)C.[CH3:16][C:17]1([CH3:45])[CH2:43][C:21]2[C:22]([C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:42])[C:39]([OH:41])=O)[CH:34]=[CH:35][CH:36]=3)=[C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[S:24][C:20]=2[C:19](=[O:44])[CH2:18]1.[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH2:50]>C(Cl)Cl>[CH3:46][N:47]([CH3:51])[CH2:48][CH2:49][NH:50][C:39](=[O:41])[C:38]([NH:37][C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([C:22]2[C:21]3[CH2:43][C:17]([CH3:16])([CH3:45])[CH2:18][C:19](=[O:44])[C:20]=3[S:24][C:23]=2[N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[CH:32]=1)=[O:42]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Isobutyl chloroformate (30 μL, 0.23 mmol) and triethylamine (30 μL, 0.23 mmol) were added to a solution of Example 292 (50 mg, 0.12 mmol) in DCM (5.0 mL) and the reaction mixture was stirred at room temperature for 1 h. N,N-Dimethylethylenediamine (60 μL, 0.58 mmol) was then added and the reaction mixture was stirred at room temperature for 72 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (pH 5.8) to give the title compound (4 mg, 6%) as a yellow solid. δH (CDCl3) 9.12 (1H, s), 8.41 (1H, br s), 7.55-7.46 (2H, m), 7.29 (1H, t, J 7.9 Hz), 7.05-7.00 (1H, m), 3.61-3.49 (6H, m), 2.90-2.77 (6H, m), 2.49 (6H, s), 2.33 (2H, s), 2.29 (2H, s), 0.90 (6H, s). LCMS (ES+) 499.3 (M+H)+.
Workup
- stirringthe reaction mixture was stirred at room temperature for 72 h
- customThe solvent was removed in vacuo
- customthe residue was purified by preparative HPLC (pH 5.8)
Sources & evidence
- ORD record
- ord-ba4712c9b4044576bd457c22a125a7f5
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324204B2
Reaction notes
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