Triethylamine → HCID 21344952, compound
Reaction equation
C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH:24]1[C:32]([O:34][CH3:35])=[O:33].[C:36]([O:40][C:41]([NH:43][C@@H:44]([CH2:48][CH3:49])[C:45](O)=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[C:36]([O:40][C:41]([NH:43][C@@H:44]([CH2:48][CH3:49])[C:45]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][C@H:24]1[C:32]([O:34][CH3:35])=[O:33])=[O:46])=[O:42])([CH3:39])([CH3:38])[CH3:37]Participants
Conditions
- Temperature
- 5 °C
Procedure
Triethylamine (3.15 ml) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (5.75 g, 22.6 mmol) were added to a solution of methyl indoline-2-carboxylate (2 g, 11.3 mmol) and N-t-butoxycarbonyl-2(S)-aminobutyric acid (2.6 g, 13.6 mmol) in methylene chloride (15 ml), at 0° C. under nitrogen. The reaction was stirred for 2 h at 5° C. and then at room temperature overnight. The mixture was filtered, the filtrate was washed with water (2×40 ml) and the combined aqueous fractions were extracted with methylene chloride. The combined organic fractions were dried and concentrated to give a residue, which was purified by chromatography on a column of silica gel, using a 7/3 petroleum ether/ethyl acetate mixture as eluent. The product was obtained in the form of a white solid.
Workup
- customat room temperature
- customovernight
- filtrationThe mixture was filtered
- washthe filtrate was washed with water (2×40 ml)
- extractionthe combined aqueous fractions were extracted with methylene chloride
- customThe combined organic fractions were dried
- concentrationconcentrated
- customto give a residue, which
- customwas purified by chromatography on a column of silica gel
- customThe product was obtained in the form of a white solid
Sources & evidence
- ORD record
- ord-c957bb91cd564307a129f82240f6e20b
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403561B1
Reaction notes
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