L-Valine → N-(1,3-Dimethylindole-2-Carbonyl)Valine
Reaction equation
CCN=C=NCCCN(C)C.[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:22])=[C:14]1[C:23]([OH:25])=O.C(Cl)Cl.[NH2:29][C@H:30]([C:34]([OH:36])=[O:35])[CH:31]([CH3:33])[CH3:32]>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:22])=[C:14]1[C:23]([NH:29][C@H:30]([C:34]([OH:36])=[O:35])[CH:31]([CH3:33])[CH3:32])=[O:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
DMAP (367 mg, 3.0 mmol) and EDAC (748 mg, 3.9 mmol) were added as solids to a solution of 1,3-dimethylindole-2-carboxylic acid (568 mg, 3.3 mmol) in DMF (5 mL), and the resultant mixture was stirred for 10 minutes under a nitrogen atmosphere at 0° C. A methylene chloride solution of the methyl ester of valine (553 mg, 3.3 mmol, in 5 mL of methylene chloride) was added to the mixture, and the mixture was first stirred for one hour at 0° C. then for 5 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution and the aqueous solution was back-extracted with ethyl acetate. The combined ethyl acetate washes were in turn washed with 5% KHSO4 solution saturated sodium bicarbonate solution (2×) and brine, dried over sodium sulfate, and concentrated to give the title product as a yellow syrup (900 mg).
Workup
- waitfor 5 hours at room temperature
- customThe reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution
- extractionthe aqueous solution was back-extracted with ethyl acetate
- washwashed with 5% KHSO4 solution saturated sodium bicarbonate solution (2×) and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-09232066fb1748d7a8d05218e6dbbc26
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877197
Reaction notes
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