Water → 7-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acid

HRID 2276706Notes

Reaction equation

HRID 2276706 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].[OH-].[K+].O>C(O)C>[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

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 90388837Ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoate

Product 1

HCID 95435387-((2-((Tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl 7-((2-((tert-butoxycarbonyl)amino)phenyl)amino)-7-oxoheptanoate (14 g, 37 mmol) in Ethanol (80 mL) was added KOH (6.2 g, 111 mmol) and water (80 mL). The mixture was stirred at room temperature for 4 hours, and then concentrated under reduce pressure. The pH value of the solution was adjusted to 4 by concentrated HCl. The resulting mixture was extracted by EtOAc (200 mL×3). The organic layers were combined and dried over Na2SO4, then concentrated to give the desired compound (12 g, yield 92.5%).

Workup

  1. concentrationconcentrated
  2. extractionThe resulting mixture was extracted by EtOAc (200 mL×3)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0549be732c5441a18a132d728a19f116
Source dataset
uspto-grants-2015_09
Patent number
US09133105B2

Reaction notes

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