4-Oxobutanoic acid → HCID 131725114, compound

HRID 586818Notes

Reaction equation

HRID 586818 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].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[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.[CH2:56]([CH:61]=O)[CH2:57][C:58]([OH:60])=[O:59]>>[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].[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[CH3:22][C:23]1[CH:32]=[C:31]([CH2:33][O:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]3([N:50]4[CH2:55][CH2:54][N:53]([CH2:61][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:52][CH2:51]4)[C:46](=[O:47])[NH:45][C:44](=[O:48])[NH:43][C:42]3=[O:49])=[CH:39][CH:40]=2)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1

Participants

3

Reactant 2

HCID 11124-Oxobutanoic acidHCID 131725107HCID 131725107, compound

Product 1

HCID 131725114HCID 131725114, compoundYield 45.1%

Procedure

Using a procedure analogous to Example 15, the product from example 14 (100 mg, 0.125 mmol) was treated with succinic semialdehyde (76.6 mg, 6.0 eq) to provide the title barbituric acid (50.0 mg, 45%). MS found: (M+H)+=546.

Sources & evidence

ORD record
ord-bea0cccc55574db98bc9540a6d83000c
Source dataset
uspto-grants-2005_08
Patent number
US06936620B2

Reaction notes

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