Lithium hydroxide, monohydrate → 7-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid

HRID 2276696Notes

Reaction equation

HRID 2276696 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90388837Ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoate

Product 1

HCID 95435387-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoate (3.7 g, 9.7 mmol) in THF/MeOH/H2O (V:V:V=4:1:1) (50 mL) were added lithium hydroxide monohydrate (1.3 g, 29.1 mmol). The mixture was stirred at room temperature for 3 hours and quenched with water (200 mL). To the solution was added 1M HCl to adjust the pH value to 2-3, then a white solid precipitated and was filtered to afford the desired compound (3.3 g, yield 96.5%).

Workup

  1. customquenched with water (200 mL)
  2. additionTo the solution was added 1M HCl
  3. customa white solid precipitated
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-674111106f3f48a1b14ebb54ece56ff2
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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