2-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile → 2-(4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile

HRID 1453059Notes

Reaction equation

HRID 1453059 reaction equation
[CH:1]1([C:6]([OH:33])([CH2:23][C:24]2[O:25][C:26]([CH3:32])([CH3:31])[O:27][C:28](=[O:30])[CH:29]=2)[C:7]#[C:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:16]#[N:17])=[C:11]([F:22])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)(CC2OC(C)(C)OC(=O)C=2)C#CC2C=CC(C3(C#N)CC3)=C(F)C=2)CCCC1>>[CH:1]1([C:6]([OH:33])([CH2:23][C:24]2[O:25][C:26]([CH3:31])([CH3:32])[O:27][C:28](=[O:30])[CH:29]=2)[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH2:18][CH3:19])([CH2:20][CH3:21])[C:16]#[N:17])=[C:11]([F:22])[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 252321552-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-2-ethyl-butyronitrileHCID 587623341-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile

Product 1

HCID 587626112-(4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-butyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile

Procedure

The desired product was prepared analogously to example A(86) step 6, substituting 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-2-ethyl-butyronitrile (0.900 g, 2.0 mmol) from step 2 above in place of 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile. Yield: 0.841 g, 92%. MS (ESI): 456 (M−H).

Sources & evidence

ORD record
ord-d1452159dbe64fe9a2d6ebda434fa64a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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