Pivaloyl chloride → HCID 131725116, compound

HRID 586820Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].FC(F)(F)C(O)=O.[CH3:22][C:23]1[CH:32]=[C:31]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]3([N:50]4[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]4)[C:46](=[O:47])[NH:45][C:44](=[O:48])[NH:43][C:42]3=[O:49])=[CH:37][CH:36]=2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.[C:56](Cl)(=[O:61])[C:57]([CH3:60])([CH3:59])[CH3:58]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].[CH3:58][C:57]([CH3:60])([CH3:59])[C:56]([N:53]1[CH2:54][CH2:55][N:50]([C:41]2([C:38]3[CH:37]=[CH:36][C:35]([O:34][CH2:33][C:31]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]=[C:23]([CH3:22])[CH:32]=4)=[CH:40][CH:39]=3)[C:46](=[O:47])[NH:45][C:44](=[O:48])[NH:43][C:42]2=[O:49])[CH2:51][CH2:52]1)=[O:61]

Participants

Reactant 2

HCID 62493Pivaloyl chloride

HCID 131725107HCID 131725107, compound

Product 1

HCID 131725116HCID 131725116, compoundYield 40%

Procedure

Using a procedure analogous to Example 26, the product from Example 14 (120 mg, 0.150 mmol) was treated with pivaloyl chloride (21.7 mg, 1.2 eq) to provide the title barbituric acid (45.0 mg, 40%). MS found: (M+H)+=544.

Sources & evidence

ORD record: ord-347cb9d3682e4778865635b1a4c7d408
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936620B2

Reaction notes

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