Water → HCID 86710437, compound

HRID 1398464Notes

Reaction equation

HRID 1398464 reaction equation
[NH2:1][C@@H:2]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:3][O:4][C:5]1[C:6]([C:22]#N)=[CH:7][C:8]2[C:17]3[C:12](=[C:13]([CH3:18])[N:14]=[CH:15][CH:16]=3)[C:11](=[O:19])[N:10]([CH3:20])[C:9]=2[CH:21]=1.[OH2:28].[OH-:29].[Na+]>C(O)C>[NH2:1][C@@H:2]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:3][O:4][C:5]1[C:6]([C:22]([OH:29])=[O:28])=[CH:7][C:8]2[C:17]3[C:12](=[C:13]([CH3:18])[N:14]=[CH:15][CH:16]=3)[C:11](=[O:19])[N:10]([CH3:20])[C:9]=2[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 73214233HCID 73214233, compound

Product 1

HCID 86710437HCID 86710437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-8-((2-amino-4-methylpentyl)oxy)-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbonitrile (450 mg, 1.235 mmol), prepared as described in Example 64, in ethanol (5 mL) and water (5 mL) was added NaOH (494 mg, 12.35 mmol). The mixture was heated to 80° C. for 12 h. The volatiles were evaporated and the residue was diluted with water The pH was adjusted to 3 using 1.5N HCl. The solution was extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (S)-8-((2-amino-4-methylpentyl)oxy)-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carboxylic acid (90 mg, 0.235 mmol, 19% crude yield) as a yellow solid. The material was carried forward without further purification. LC/MS (ESI) m/e 384.1 [(M+H)+, calcd for C21H26N3O4 384.2]; LC/MS retention time (method D): tR=0.72 min.

Workup

  1. customThe volatiles were evaporated
  2. additionthe residue was diluted with water The pH
  3. extractionThe solution was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-950b01d6e44d4e9db84bd6cb7bfae729
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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