Sodium hydride → HCID 178460580, compound

HRID 1766927Notes

Reaction equation

HRID 1766927 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[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][C:54]=1[C:55](Cl)=[O:56])([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[CH:61]=[CH:60][C:59]([CH3:62])=[CH:58][C:54]=1[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:56])([O:44][CH2:41][CH:42]=[CH2:43])=[O:46])[CH:49]=[CH2:50]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 211104492-[[Bis(allyloxy)phosphoryl]oxymethyl]-5-methylbenzoyl chlorideHCID 178462432HCID 178462432, compound

Product 1

HCID 178460580HCID 178460580, compoundYield 43%

Procedure

According to a similar procedure to that described in Example 4-(6), 4-methoxybenzyl 2-[[bis(allyloxy)phosphoryl]oxymethyl]-5-methylbenzoate (690 mg, 1.54 mmol) was treated with trifluoroacetic acid to afford 2-[[bis(allyloxy)phosphoryl]oxymethyl]-5-methylbenzoic acid as a crude product. According to a similar procedure to that described in Example 4-(6), the above product was treated with oxalyl chloride and N,N-dimethylformamide to afford 2-[[bis(allyloxy)phosphoryl]oxymethyl]-5-methylbenzoyl chloride as a crude product. 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 (670 mg, 1.23 mmol) described in Reference example 1 was treated with sodium hydride and then reacted with the crude 2-[[bis(allyloxy)phosphoryl]oxymethyl]-5-methylbenzoyl chloride (the whole amount) obtained above to afford, after purification by column chromatography, the title compound (448 mg, 43% yield) as a pale yellow, candy-like material.

Workup

  1. customobtained above
  2. customto afford
  3. customafter purification by column chromatography

Sources & evidence

ORD record
ord-f68511f378f54d6d8071fc75df9647b5
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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