Triethylamine → HCID 131723263, compound

HRID 2185684Notes

Reaction equation

[CH2:1]([NH:5][C:6]([CH:8]1[C:16]([CH3:18])([CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH2:19]([O:26][C:27]([NH:29][C@@H:30]([CH2:34][CH3:35])[C:31](O)=[O:32])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([NH:5][C:6]([CH:8]1[C:16]([CH3:17])([CH3:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]1[C:31](=[O:32])[C@@H:30]([NH:29][C:27]([O:26][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:28])[CH2:34][CH3:35])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

3,3-Dimethylindoline-2(R/S)-carboxylic acid butylamide (1.000 g, 4.08 mmol) and N-benzyloxycarbonyl-2(S)-aminobutyric acid (1.451 g, 6.12 mmol) were dissolved in dry tetrahydrofuran (25 ml). The solution was cooled to 0° C. and triethylamine (2.44 ml, 13.78 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (2.338 g, 9.183 mmol) were added. The mixture was stirred at room temperature for 22 hours and ethyl acetate (40 ml) was then added, and the mixture was washed with 3N hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (50 ml) and dried over sodium sulphate. After removing the solvent, several successive purifications by chromatography on a column of silica gel gave the product in the form of an off-white solid.

Workup

washthe mixture was washed with 3N hydrochloric acid (3×50 ml), 5% sodium bicarbonate (3×50 ml) and water (50 ml)
dry with materialdried over sodium sulphate
customAfter removing the solvent, several successive purifications by chromatography on a column of silica gel
customgave the product in the form of an off-white solid

Sources & evidence

ORD record: ord-f36c178a9da14e7bb913f65532606823
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403561B1

Reaction notes

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