Triethylamine → HCID 131723262, compound
Reaction equation
C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH2:23]([NH:27][C:28]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([O:39][CH3:40])[CH:36]=2)[NH:31]1)=[O:29])[CH2:24][CH2:25][CH3:26].[CH2:41]([O:48][C:49]([NH:51][C@H:52]([C:54](O)=[O:55])[CH3:53])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[CH2:23]([NH:27][C:28]([CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([O:39][CH3:40])[CH:36]=2)[N:31]1[C:54](=[O:55])[C@H:52]([CH3:53])[NH:51][C:49]([O:48][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:50])=[O:29])[CH2:24][CH2:25][CH3:26]Participants
6
Procedure
Triethylamine (1.12 ml, 8 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (0.815 g, 3.2 mmol) were added to a cooled (0° C.) solution of 5-methoxyindoline-2(R/S)-carboxylic acid butylamide (0.500 g, 2.01 mmol) and N-benzyloxycarbonyl-L-alanine (0.4956 g, 2.22 mmol) dissolved in dichloromethane (25 ml), under nitrogen. The mixture was stirred at room temperature for 22 hours. It was then washed with 10% citric acid (3×30 ml), 5% NaHCO3 (3×30 ml) and water (30 ml). The organic phase was dried and concentrated and the residue was purified by chromatography on a column of silica gel, using a 1/1 petroleum ether/ethyl acetate mixture as eluent. A white solid was obtained.
Workup
- washIt was then washed with 10% citric acid (3×30 ml), 5% NaHCO3 (3×30 ml) and water (30 ml)
- customThe organic phase was dried
- concentrationconcentrated
- customthe residue was purified by chromatography on a column of silica gel
- customA white solid was obtained
Sources & evidence
- ORD record
- ord-0403582fe69e4de799e68519488194f1
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403561B1
Reaction notes
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