Methyl iodide → HCID 18652324, compound

HRID 1492156Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:16][C:17]2[CH:28]=[CH:27][C:20]3[NH:21][C:22](=[O:26])[C@@H:23]([CH3:25])[O:24][C:19]=3[CH:18]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:29]I>>[F:1][C:2]1[CH:3]=[C:4]([S:16][C:17]2[CH:28]=[CH:27][C:20]3[N:21]([CH3:29])[C:22](=[O:26])[C@@H:23]([CH3:25])[O:24][C:19]=3[CH:18]=2)[CH:5]=[C:6]([C:8]2([O:14][CH3:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[CH:7]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 18652326HCID 18652326, compound

Product 1

HCID 18652324HCID 18652324, compoundYield 42%

Procedure

Using a similar procedure to that described in Example 16, (R)(-)-4-[5-fluoro-3-(2-methyl-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-7-ylthio)phenyl]-4-methoxytetrahydropyran was reacted with methyl iodide to give (R)-(-)-4-[5-fluoro-3-(2,4-dimethyl-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-7-ylthio)phenyl]-4-methoxytetrahydropyran in 42% yield, m.p. 107°-109° C. Specific Rotation: [alpha]D =-36.8° (methylene chloride, c=1 g/100 ml, temp.=25° C).

Sources & evidence

ORD record: ord-44de2e05fe79413dbdf763b66ce177f4
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05373007

Reaction notes

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