Hydrochloric Acid → 6-[4-(2-hydroxybenzoylamino)benzoylamino]hexanoic acid
Reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[O:7])=[CH:4][CH:3]=1.[OH:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].C(N(CC)CC)C.[OH-].[Na+].Cl>C(#N)C>[OH:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])=[CH:4][CH:3]=1)=[O:24]Participants
Procedure
To a solution of 2.81 g (10.64 mmol) of methyl 6-(4-aminobenzoylamino)hexanoate dissolved in 50 ml of acetonitrile, very slowly add 1.42 g (9.10 mmol) of 2-hydroxybenzoyl chloride dissolved in 5 ml of acetonitrile. Then add 0.92 g (9.10 mmol) of triethylamine and keep the reaction mixture at room temperature for 24 hours. Eliminate the solvent at low pressure, add 30 ml of 10% NaOH to the crude product and continue stirring the mixture until the solid has completely disappeared. Immediately acidify with concentrated hydrochloric acid, filter the resulting solid and wash several times with water. Purify the reaction product by recrystallization (EtOH/H2O). This yields 1.11 g (33%) of 6-[4-(2-hydroxybenzoylamino)benzoylamino]hexanoic acid as a white solid.
Workup
- customat room temperature
- customfor 24 hours
- filtrationfilter the resulting solid
- washwash several times with water
- customPurify the reaction product
- customby recrystallization (EtOH/H2O)
Sources & evidence
- ORD record
- ord-50da7151beae4f9a83a56f2128781fe2
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462735B2
Reaction notes
Loading…