Triphenylphosphine → (Z)-(S)-4-(4-fluorobenzyl)-2-[1-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-6-methylmorpholin-3-one

HRID 1436132Notes

Reaction equation

HRID 1436132 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:12][CH:11]([CH3:13])[O:10][C@H:9](O)[C:8]2=[O:15])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[N:50]1[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]1)[CH:45]=O>>[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH2:12][C@H:11]([CH3:13])[O:10]/[C:9](=[CH:45]\[C:44]3[CH:47]=[CH:48][C:49]([N:50]4[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]4)=[C:42]([F:41])[CH:43]=3)/[C:8]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 69005909(S)-4-(4-fluorobenzyl)-2-hydroxy-6-methylmorpholin-3-oneHCID 707008423-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 57938669(Z)-(S)-4-(4-fluorobenzyl)-2-[1-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene]-6-methylmorpholin-3-one

Procedure

9.06 mg of the title compound was obtained from (S)-4-(4-fluorobenzyl)-2-hydroxy-6-methylmorpholin-3-one, thionyl chloride, triphenylphosphine, and 3-fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde in the same manner as in Example 5.

Sources & evidence

ORD record
ord-8c99a2c123ae4f7b9c50d66c2611e86d
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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