Hydrochloric Acid → HCID 86701773, compound

HRID 2174129Notes

Reaction equation

HRID 2174129 reaction equation
[C:1]([C:3]([C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH3:20])=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:8])[C:4]([O:6]C)=[O:5])#[N:2].[OH-].[K+].Cl>CCO.O.C(OCC)(=O)C>[C:24]([O:23][C:21]([N:13]1[C:14]2[C:10](=[C:9]([C:3]([C:1]#[N:2])([CH3:8])[C:4]([OH:6])=[O:5])[C:17]([O:18][CH3:19])=[CH:16][C:15]=2[CH3:20])[CH:11]=[CH:12]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86701772HCID 86701772, compound

Product 1

HCID 86701773HCID 86701773, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(±)-tert-Butyl 4-(2-cyano-1-methoxy-1-oxopropan-2-yl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 155-D) (0.35 g, 0.940 mmol) was dissolved in EtOH (4.70 ml), cooled to 0° C. and added 10% KOH (2.64 ml, 4.70 mmol) and stirred for 1 hour. At this point, the reaction was placed in an ice bath and quenched with 1 N HCl (4.70 ml, 4.70 mmol). The reaction was diluted with water and ethyl acetate. The layers were separated and the ethyl acetate layer was removed, dried over Na2SO4 and concentrated to obtain the title compound which was used directly in the next reaction without purification. MS (ESI+) m/z 359.4 (M+H).

Workup

  1. customAt this point, the reaction was placed in an ice bath
  2. customThe layers were separated
  3. customthe ethyl acetate layer was removed
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31524c7067bb4a509061eecafb7bb3dc
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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