Sodium Iodide → HCID 86655160, compound

HRID 391253Notes

Reaction equation

Br[CH:2]([CH2:15][CH:16]1[CH2:18][CH2:17]1)[C:3]([O:5][C@@H:6]([CH3:14])[C:7](=[O:13])[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:4].[Na+].[I-].C(N(CC)CC)C.[CH3:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O1CCCC1>[CH3:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH:34][CH:2]([CH2:15][CH:16]2[CH2:18][CH2:17]2)[C:3]([O:5][C@@H:6]([CH3:14])[C:7](=[O:13])[N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:4])=[CH:32][CH:31]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To (1S)-1-methyl-2-oxo-2-tetrahydro-1-H-1-pyrrolylethyl 2-bromo-3-cyclopropylpropanoate (418 mg, 1.3 mmol), NaI (198 mg, 1.3 mmol), triethylamine (214 g, 2.1 mmol) and tetrahydrofuran (5 mL) were added. To the solution, p-methoxyaniline (211 mg, 1.7 mmol) and tetrahydrofuran (3 mL) were added. The mixture was stirred at room temperature for 24 hours and further at 40° C. for 20 hours. To the mixture, a saturated sodium sulfite aqueous solution and ethyl acetate were added for extraction. The obtained extract was dried with anhydrous magnesium sulfate, and the solvent was removed away under reduced pressure. The residue was purified with silica gel chromatography to obtain 270 mg of the target compound (yield: 57%, The diastereo ratio calculated by NMR analysis was 92:8.).

Workup

extractionThe obtained extract
dry with materialwas dried with anhydrous magnesium sulfate
customthe solvent was removed away under reduced pressure
customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record: ord-d1d229d964ef4fa29c60f9e6b0bff0b3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383833B2

Reaction notes

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