Tetrahydrofuran → HCID 178460585, compound

HRID 1766885Notes

Reaction equation

HRID 1766885 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:38])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C@H:10]([S:12][C@@H:13]1[CH2:18][O:17][C@@H:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[F:31])[O:15][CH2:14]1)[CH3:11].[H-].[Na+].[CH2:41]([O:44][P:45]([O:51][CH2:52][CH2:53][C:54]([CH3:58])([CH3:57])[CH2:55]Cl)([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH:42]=[CH2:43].[O:59]1CCCC1>>[CH2:41]([O:44][P:45]([O:51][CH2:52][CH2:53][C:54]([CH3:58])([CH3:57])[C:55]([O:38][C@:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C@H:10]([S:12][C@@H:13]1[CH2:18][O:17][C@@H:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[F:31])[O:15][CH2:14]1)[CH3:11])=[O:59])([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH:42]=[CH2:43]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 211104624-[[Bis(allyloxy)phosphoryl]oxy]-2,2-dimethylbutyl chlorideHCID 178462432HCID 178462432, compound

Product 1

HCID 178460585HCID 178460585, compoundYield 15%

Procedure

According to a similar procedure to that described in Example 1-(12), 4-[(1E,3E)-4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-1,3-butadienyl]-3-fluorobenzonitrile (1.09 g, 2.0 mmol) described in Reference example 1, sodium hydride (55% dispersion in mineral oil; 104.7 mg, 2.4 mmol), and 4-[[bis(allyloxy)phosphoryl]oxy]-2,2-dimethylbutyl chloride were reacted in tetrahydrofuran (10 ml) and the reaction mixture was worked up to afford, after extraction, the title compound as a crude oil. The crude oily product was subjected to chromatography on a silica gel (75 g) column (eluent; ethyl acetate:hexane=2:1˜3:1) to afford the title compound (238.8 mg, 15% yield) as a pale yellow amorphous solid.

Workup

  1. customto afford
  2. extractionafter extraction

Sources & evidence

ORD record
ord-dcac95bd96cd43f6a24bca426b983a16
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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