Hydrochloric Acid → 4-[(Boc-amino)methyl]-phthalic acid

HRID 2080728Notes

Reaction equation

HRID 2080728 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:5](=[CH:10][C:11]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7].[OH-].[Na+].Cl>CO>[C:19]([O:18][C:16]([NH:15][CH2:14][C:11]1[CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4](=[CH:13][CH:12]=1)[C:3]([OH:23])=[O:2])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669416434-(t-butoxycarbonylamino-methyl)-phthalic Acid Dimethyl Ester

Product 1

HCID 230792094-[(Boc-amino)methyl]-phthalic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (76.4 mg) obtained in Example 7-3 was dissolved in methanol (4.5 ml). A 1 mol/l sodium hydroxide aqueous solution (2.3 ml) was dropped in this solution and the whole was stirred at room temperature for 2 hours. The solution was neutralized by addition of 1 mol/l hydrochloric acid (2.3 ml). The residue obtained by distilling the solvent off was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (65.3 mg) as a pale-yellow oily substance.

Workup

  1. customThe residue obtained
  2. distillationby distilling the solvent
  3. customoff was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-db6706007da844fab7ce6ccacd1733df
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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