Sodium hydride → HCID 178460583, compound

HRID 1766944Notes

Reaction equation

HRID 1766944 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][C:53]1[C:54]([C:58](Cl)=[O:59])=[CH:55][O:56][CH:57]=1)([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH:42]=[CH2:43]>>[CH2:48]([O:47][P:45]([O:51][CH2:52][C:53]1[C:54]([C:58]([O:38][C@:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([CH2:32][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)[C@H:10]([S:12][C@@H:13]2[CH2:18][O:17][C@@H:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]3[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=3[F:31])[O:15][CH2:14]2)[CH3:11])=[O:59])=[CH:55][O:56][CH:57]=1)([O:44][CH2:41][CH:42]=[CH2:43])=[O:46])[CH:49]=[CH2:50]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 21110467HCID 21110467, compoundHCID 178462432HCID 178462432, compound

Product 1

HCID 178460583HCID 178460583, compoundYield 70%

Procedure

According to a similar procedure to that described in Example 13-(2), 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 (690.5 mg, 1.27 mmol) described in Reference example 1, sodium hydride (55% dispersion in mineral oil; 66.5 mg, 1.52 mmol), and crude 4-[[bis(allyloxy)phosphoryl]oxymethyl]-3-furoyl chloride were reacted, and the reaction mixture was worked up to afford, after extraction, the title compound as a crude oil. The crude product was subjected to chromatography on a silica gel (30 g) column (eluent; ethyl acetate:hexane=2:1˜9:1) to afford the title compound (740.8 mg, 70% yield) as a colorless amorphous solid.

Workup

  1. customwere reacted
  2. customto afford
  3. extractionafter extraction

Sources & evidence

ORD record
ord-bb7058487fb548b8b96982fcd8824e28
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

Loading…