Hydrochloric Acid → 4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-5-vinyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

HRID 1481775Notes

Reaction equation

HRID 1481775 reaction equation
C([O:5][C:6]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[CH:22]3)[C:16]([CH:29]=[CH2:30])=[C:15]([O:31]C(C)(C)C)[C:7]=1[C:8]([O:10]C(C)(C)C)=[O:9])(C)(C)C.Cl>O1CCOCC1>[OH:31][C:15]1[CH:16]([CH:29]=[CH2:30])[CH:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[CH:22]3)[NH:18][C:6](=[O:5])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89422958tert-butyl 2,4-di-tert-butoxy-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate

Product 1

HCID 894229324-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-5-vinyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Into a solution of tert-butyl 2,4-di-tert-butoxy-6-(1-methyl-1H-indol-5-yl)-5-vinylnicotinate (44 mg, 0.092 mmol) in dioxane (1.0 mL) was added a solution of HCl in dioxane (4.0 M×1.0 mL, 4.0 mmol). After 1 min, the mixture was evaporated to dryness. The residue was treated with ether and filtered. The solid was collected as 4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-5-vinyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (26 mg, 97%).

Workup

  1. customthe mixture was evaporated to dryness
  2. additionThe residue was treated with ether
  3. filtrationfiltered
  4. customThe solid was collected as 4-hydroxy-6-(1-methyl-1H-indol-5-yl)-2-oxo-5-vinyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (26 mg, 97%)

Sources & evidence

ORD record
ord-9210cd3d7f47418583558cfaad00a408
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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