Dimethylformamide → HCID 15127717, compound

HRID 1596598Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CI.[H-].[Na+].[CH3:25]N(C)C=O>O1CCCC1>[C:1]([N:8]([CH3:25])[C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Following the procedure of Boger and Yohannes (J. Org. Chem. 53, 487 (1988), a solution of N-BOC-4-iodophenylalanine (391 mg, 1 mmol) and methyl iodide (156 μL, 2.5 mmol) in tetrahydrofuran (5 mL) at 0° C. was added 60% sodium hydride in oil suspension (100 mg, 2.5 mmol). The resulting mixture was stirred at 0° C. for 1 hr and then at room temperature for 16 hr. Added dimethylformamide (1 mL) and additional methyl iodide (156 μL, 2.5 mmol) and 60% sodium hydride (100 mg, 2.5 mmol) and heated at 75° C. overnight. The reaction was worked up as described in the reference to yield N-BOC-N-methyl-4-iodophenylalanine.

Workup

waitat room temperature for 16 hr

Sources & evidence

ORD record: ord-56d01e10a97d407fadb72bc4243771ae
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291511B1

Reaction notes

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