1-Iodopropane → HCID 69101078, compound

HRID 394039Notes

Reaction equation

[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@@H:40]2[CH2:45][CH2:44][CH2:43][N:42]([CH2:46][CH2:47][CH3:48])[CH2:41]2)=[O:37])=[O:30])[CH2:3]1.[CH2:49]([I:52])[CH2:50][CH3:51]>C(Cl)(Cl)Cl>[I-:52].[OH:1][C@H:2]1[CH2:6][N:5]([C:7](=[O:28])[CH2:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@H:4]([C:29]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[C:36]([NH:38][CH2:39][C@@H:40]2[CH2:45][CH2:44][CH2:43][N+:42]([CH2:49][CH2:50][CH3:51])([CH2:46][CH2:47][CH3:48])[CH2:41]2)=[O:37])=[O:30])[CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 4.9 mg of (2R)-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl)carbonyl-N-{((3S)-1-propyl-3-piperidyl)methyl}pyrrolidine-2-carboxamide, 1 ml of propyl iodide was added at room temperature, followed by 15 hours' stirring at 100° C. under heating. The reaction liquid was diluted with chloroform, the solvent was distilled off under reduced pressure, and the resulting residue was purified with preparative thin-layer chromatography (aluminium oxide 60F254, Art 5713 (Merck), chloroforom/methanol=18/1) to provide 4.1 mg of the title compound as a pale yellow solid.

Workup

temperatureunder heating
customThe reaction liquid
distillationthe solvent was distilled off under reduced pressure
customthe resulting residue was purified with preparative thin-layer chromatography (aluminium oxide 60F254, Art 5713 (Merck), chloroforom/methanol=18/1)

Sources & evidence

ORD record: ord-cac6244da6d64f7ba7c9f6d48a51bca4
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809108B1

Reaction notes

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