Methyl iodide → HCID 44592056, compound

HRID 2384593Notes

Reaction equation

[CH:1]1[C:6]2[CH2:7][C@H:8]3[N:13]([CH2:14][CH:15]4[CH2:17][CH2:16]4)[CH2:12][CH2:11][C@:10]45[C@H:18]([C:20]([CH2:22][CH2:23][C@@:9]34[OH:24])=[O:21])[O:19][C:4]([C:5]=25)=[C:3]([OH:25])[CH:2]=1.[I:26][CH3:27]>CC(C)=O>[CH3:27][N+:13]1([CH2:14][CH:15]2[CH2:17][CH2:16]2)[C@@H:8]2[CH2:7][C:6]3=[CH:1][CH:2]=[C:3]([OH:25])[C:4]4[O:19][C@H:18]5[C:20]([CH2:22][CH2:23][C@:9]2([OH:24])[C@:10]5([C:5]=43)[CH2:11][CH2:12]1)=[O:21].[I-:26]

Participants

Conditions

Temperature: 70 °C

Procedure

Naltrexone (1, 30 mg, 0.062 mmol) dissolved in 5 mL of dry acetone was added to iodomethane (0.04 mL, 0.62 mmol) in a reaction tube. The reaction tube was sealed and heated at 70° C. for four days. A white precipitate formed over the course of reaction. At the end of the reaction, the mixture was cooled and filtered and the precipitate was washed with cold acetone. The white precipitate was crystallized from methanol-ether to obtain the desired product 2 as a crystalline salt in 41% yield: mp 215-216° C. 1H NMR (DMSO-d6, 500 MHz) δ 9.52 (s, 1H) 6.67 (s, 2H), 6.35 (s, 1H), 4.90 (s, 1H), 4.02 (s, 1H), 3.91 (m, 2H), 3.62 (s, 3H), 3.52 (d, J=19.5 Hz, 1H), 3.05 (m, 1H), 2.92 (m, 2H), 2.76 (m, 2H), 2.10 (m, 1H), 1.97 (m, 1H), 1.59 (m, 2H), 1.22 (m, 1H), 0.77 (m, 1H), 0.70 (m, 1H), 0.61 (m, 1H), 0.37 (m, 1H). MS m/z 356 [(M−I−)+]. Anal. Calcd for C21H26IN4.0.75H2O: C, 50.77; H, 5.58; N, 2.82. Found C, 50.49; H, 5.70; N, 2.71.

Workup

customThe reaction tube was sealed
customA white precipitate formed over the course of reaction
customAt the end of the reaction
temperaturethe mixture was cooled
filtrationfiltered
washthe precipitate was washed with cold acetone
customThe white precipitate was crystallized from methanol-ether

Sources & evidence

ORD record: ord-541c66cdcda34c8c9d7ccfebf947ed67
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263807B2

Reaction notes

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