Hydrochloric Acid → HCID 71281737, compound

HRID 1481767Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:17]([C:18]2[NH:23][C:22](=[O:24])[C:21]([C:25]([O:27]C)=[O:26])=[C:20]([OH:29])[C:19]=2[CH2:30][CH3:31])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[I-].Cl>CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:17]([C:18]2[NH:23][C:22](=[O:24])[C:21]([C:25]([OH:27])=[O:26])=[C:20]([OH:29])[C:19]=2[CH2:30][CH3:31])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate (0.0387 g, 0.09 mmol) in EtOAc (0.5 mL) was added LiI (0.0360 g, 0.27 mmol). The reaction mixture was stirred and heated at 60° C. for 1 h until complete consumption of starting material was observed. The mixture was then cooled to room temperature and acidified with aqueous HCl (1M, 1.0 mL) to pH˜2. The product was extracted with EtOAc (3×3 mL). The organic phase was dried over Na2SO4. Upon removal of the solvent 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid was obtained as a yellow foam (0.0352 g, 94%).

Workup

temperatureThe mixture was then cooled to room temperature
extractionThe product was extracted with EtOAc (3×3 mL)
dry with materialThe organic phase was dried over Na2SO4
customUpon removal of the solvent 6-(4-(benzyloxy)-1-methyl-1H-indol-5-yl)-5-ethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Sources & evidence

ORD record: ord-990bc55b43fd45f191da84ae2e92d7e8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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