Methyl iodide → HCID 86622307, compound

HRID 501665Notes

Reaction equation

[CH2:1]([CH:4]([CH2:16][CH2:17][CH3:18])[C:5]([NH:7][C@@H:8]([CH2:13][CH:14]=[CH2:15])[C:9]([O:11][CH3:12])=[O:10])=[O:6])[CH2:2][CH3:3].I[CH3:20].[H-].[Na+]>C1COCC1>[CH3:20][N:7]([C@@H:8]([CH2:13][CH:14]=[CH2:15])[C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:6])[CH:4]([CH2:1][CH2:2][CH3:3])[CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Step A (2): (S)-Methyl 2-(2-propylpentanamido)pent-4-enoate (852 mg, 3.34 mmol) from Step A (1) was dissolved in THF (20 mL). Iodomethane (620 μL, 10 mmol) was added and resulting mixture chilled to 0° C. Sodium hydride (120 mg, 5.00 mmol) was added and the ice-bath was removed. After 75 min, the reaction was chilled again to 0° C. and quenched with aqueous 1 N HCl. The slurry was poured into H2O, and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography to give (S)-methyl 2-(N-methyl-2-propylpentanamido)pent-4-enoate 230 mg (26% yield). LC-MS (M+H)+=270.22. 1H NMR (300 MHz, CDCl3) δ 0.78-0.90 (m, 5H) 1.10-1.41 (m, 6H) 1.49-1.69 (m, 3H) 2.36-2.50 (m, 1H) 2.60-2.79 (m, 2H) 2.92 (s, 3H) 3.67 (s, 3H) 4.96-5.12 (m, 2H) 5.29 (dd, J=10.98, 4.76 Hz, 1H) 5.58-5.77 (m, 1H).

Workup

customresulting mixture
customthe ice-bath was removed
temperaturethe reaction was chilled again to 0° C.
customquenched with aqueous 1 N HCl
additionThe slurry was poured into H2O
extractionextracted with EtOAc (3×200 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b5dfea9f8943459a9a36bd9a3fe3434a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772221B2

Reaction notes

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