Hydrochloric Acid → 2-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid
Reaction equation
[C:1]([NH:24][CH:25]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:26]([O:28]C)=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22].[OH-].[Na+].Cl>CO>[C:1]([NH:24][CH:25]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:26]([OH:28])=[O:27])(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoate (610 mg, 1.34 mmol) in MeOH (15 mL) was added 2 M NaOH (30 mL). The reaction mixture was heated (50° C., 16 h), cooled (RT), and acidified with 2 M HCl to pH=1. The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude product was purified by silica chromatography, (MeOH:DCM, 0-10%) to afford 2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanoic acid (0.51 g, 89%) as a light yellow solid. Mass calculated for C28H43NO3=441.65. found: [M+H]+=442.1.
Workup
- temperaturecooled (RT)
- extractionThe mixture was extracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica chromatography, (MeOH:DCM, 0-10%)
Sources & evidence
- ORD record
- ord-27e3c9ae9c3e41c68db30e4dad18a29f
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09272984B2
Reaction notes
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