Sodium Hydroxide → 4-[([(Benzyloxy)carbonyl]{4-[(tert-butoxycarbonyl)amino]butyl}amino)methyl]benzoic acid

HRID 68625Notes

Reaction equation

HRID 68625 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=1)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=1)[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67163472HCID 67163472, compound

Product 1

HCID 671635874-[([(Benzyloxy)carbonyl]{4-[(tert-butoxycarbonyl)amino]butyl}amino)methyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound 4 (1.13 g) in methanol (4 mL), an aqueous 2N sodium hydroxide solution (4 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated. The obtained residue was added by 2N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated to obtain the title compound having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe obtained residue was added by 2N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afbcb5a5402d41c8b65215815e8b53b3
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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