Hydrochloric Acid → 5-(2-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoic acid

HRID 85360Notes

Reaction equation

HRID 85360 reaction equation
[C:1]([NH:24][CH:25]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([OH:39])=[C:33]([CH:38]=1)[C:34]([O:36]C)=[O:35])=[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]([CH2:40][CH:41]([CH3:42])[CH3:43])[C:26]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([OH:39])=[C:33]([CH:38]=1)[C:34]([OH:36])=[O:35])=[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

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67174625HCID 67174625, compound

Product 1

HCID 671737285-(2-Docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoic acidYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
47.5 °C

Procedure

To a solution of methyl 5-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoate (155 mg, 0.26 mmol) in MeOH (3 mL) was added 2M aqueous NaOH (5 mL). The mixture was heated (45-50° C., 16 h), and then cooled to RT. 2M aqueous HCl was added dropwise to adjust to pH 1. The mixture was then extracted by EtOAc (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (MeOH/DCM, 0-10%) to afford of 5-(2-docosa-4,7,10,13,16,19-hexaenamido-4-methylpentanamido)-2-hydroxybenzoic acid as light yellow oil (92 mg, 61%). Mass calculated for C35H48N2O5=576.77; found: [M+H]+=577.3.

Workup

  1. temperaturecooled to RT
  2. extractionThe mixture was then extracted by EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography (MeOH/DCM, 0-10%)

Sources & evidence

ORD record
ord-a82fe3b403a94d5e96617e2b17eda84e
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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