Lithium Hydroxide → HCID 131721676, compound

HRID 378144Notes

Reaction equation

HRID 378144 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:17]([NH:19][CH2:20][C:21]([NH:23][CH:24]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH2:25][C:26]([O:28]CC)=[O:27])=[O:22])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>O.C(#N)C>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:12]=[C:13]([C:17]([NH:19][CH2:20][C:21]([NH:23][CH:24]([C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH2:25][C:26]([OH:28])=[O:27])=[O:22])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 22608684HCID 22608684, compound

Product 1

HCID 131721676HCID 131721676, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
25 °C

Procedure

The compound of Example 107 (500 mg, 0.095 mmol) was dissolved in water/acetonitrile (1:1), followed by the addition of lithium hydroxide (100 mg, 0.4 mmol). The reaction mixture was stirred at 25° C., and monitored by HPLC. After complete hydrolysis (1-2 hours) trifluoroacetic acid was added until pH=2. The product was purified by reverse phase chromatography (water/acetonitrile) to result in a white solid (350 mg). MS and 1H-NMR were consistent with 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-55c458dd19ba482da9dc0df1d593aa38
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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