Ethanol → HCID 58859156, compound

HRID 1349469Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][NH:6][C:7]([C:9]1O[CH:11]=[C:12]([CH:24]([OH:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:8].C(O)C.[CH3:36][O:37][CH:38]([O:41][CH3:42])[CH2:39][NH2:40]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][NH:6][C:7]([C:9]1[N:40]([CH2:39][CH:38]([O:41][CH3:42])[O:37][CH3:36])[CH:11]=[C:12]([CH:24]([OH:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-benzyloxy-5-(1-hydroxy-2,2-dimethylpropyl)-4-oxo-4H-pyran-2-carboxylic acid 3-chlorobenzylamide (0.22 g) in tetrahydrofuran (1.5 ml)-ethanol (1.5 ml) was added aminoacetaldehyde dimethyl acetal (0.16 ml) and the mixture was stirred at 60° C. for 24 hr. The solvent was evaporated and purified by silica gel column chromatography (ethyl acetate:hexane=1:1-ethyl acetate) to give 3-benzyloxy-1-(2,2-dimethoxyethyl)-5-(1-hydroxy-2,2-dimethylpropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid 3-chlorobenzylamide (198 mg).

Workup

customThe solvent was evaporated
custompurified by silica gel column chromatography (ethyl acetate:hexane=1:1-ethyl acetate)

Sources & evidence

ORD record: ord-9da79416d9ee41bbb5de4a6e6121eeaf
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211572B2

Reaction notes

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