Sodium Iodide → HCID 67459904, compound

HRID 554003Notes

Reaction equation

C(N(C(C)C)CC)(C)C.[I-].[Na+].[NH2:12][CH:13]([C:28]1[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=1)[CH2:14][N:15]([C:24]([O:26][CH3:27])=[O:25])[CH2:16][CH:17](Cl)[C:18]([O:20][CH2:21][CH3:22])=[O:19].O.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:27][O:26][C:24]([N:15]1[CH2:14][CH:13]([C:28]2[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=2)[NH:12][CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16]1)=[O:25]

Participants

Conditions

Temperature: 80 °C

Procedure

IPEA (1.85 mL) and sodium iodide (795 mg) were added to a solution of ethyl 3-{[2-amino-2-(3,4,5-trifluorophenyl)ethyl]methoxycarbonylamino}-2-chloropropionate (2.03 g) in THF (20 mL), and the reaction solution was stirred at 80° C. for four hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane->heptane:ethyl acetate=2:1) to obtain 991 mg of the title compound. The property value of the compound is as follows.

Workup

waitThe reaction solution was left
temperatureto cool to room temperature
customthe organic layer was separated
dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (heptane->heptane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-809b54eb25eb4102bb86360f61594d70
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048878B2

Reaction notes

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