Lithium Hydroxide → HCID 178514382, compound

HRID 378140Notes

Reaction equation

HRID 378140 reaction equation
[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:6]=[C:7]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[O:16])=[O:12])[CH:8]=[CH:9][CH:10]=1.[OH-].[Li+].FC(F)(F)C(O)=O>O.C(#N)C>[NH2:1][N:2]=[CH:3][NH:4][C:5]1[CH:6]=[C:7]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:16])=[O:12])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 178472099HCID 178472099, compound

Product 1

HCID 178514382HCID 178514382, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

The compound of Example 96 (500 mg) was dissolved in water/acetonitrile (1:1) followed by the addition of lithium hydroxide (200 mg). The reaction mixture was stirred at 25° C., and monitored by HPLC. After complete hydrolysis (1-2 hours) triflouroacetic acid was added until pH=2. The product was purified by reverse phase chromatography (water/acetonitrile) to result in 375 mg of a white solid. MS and 1H-NMR were consistent with the proposed structure.

Workup

  1. additionwas added until pH=2
  2. customThe product was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-bc26469fb7244d57b70029294fe067d8
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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