Hydrochloric Acid → HCID 66691255, compound

HRID 1922573Notes

Reaction equation

HRID 1922573 reaction equation
[C:1]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([OH:35])=[C:29]([CH:34]=1)[C:30]([O:32]C)=[O:31])(=[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].Cl>[OH-].[Na+].CO>[C:1]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([OH:35])=[C:29]([CH:34]=1)[C:30]([OH:32])=[O:31])(=[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 2

HCID 313Hydrochloric AcidHCID 67174747HCID 67174747, compound

Product 1

HCID 66691255HCID 66691255, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-docosa-4,7,10,13,16,19-hexaenamido-2-hydroxybenzoate (0.1 g, 0.2 mmol) in 2N NaOH (5 mL) and CH3OH (2.5 mL) was stirred (50° C., 24 h). The mixture was cooled and acidified to pH 1 with 2N aq. HCl, then extracted with EtOAc (3×10 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography (CH2Cl2-EtOAc, 20:1 to 1:1) to afford 5-docosa-4,7,10,13,16,19-hexaenamido-2-hydroxybenzoic acid as a white solid (90.4 mg, yield: 90%). Mass calculated for C29H37NO4=463.61; found: [M+H]+=464.3.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica chromatography (CH2Cl2-EtOAc, 20:1 to 1:1)

Sources & evidence

ORD record
ord-90a9d2709bf04755828a928f7c06ac72
Source dataset
uspto-grants-2012_05
Patent number
US08173831B2

Reaction notes

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