Hydrochloric Acid → HCID 11211082, compound

HRID 2121088Notes

Reaction equation

HRID 2121088 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[OH-].[Na+].[Cl:16][C:17]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:19]([C:20]([O-])=[O:21])[C:18]=1[OH:27].Cl>O1CCOCC1>[Cl:16][C:17]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:19]([C:20]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:21])[C:18]=1[OH:27]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium Hydroxide2×HCID 8315010-Aminodecanoic acidHCID 178524409HCID 178524409, compound

Product 1

HCID 11211082HCID 11211082, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A slurry of 3.0 g of (16.0 mmol, 1.1 eq) 10-aminodecanoic acid, 9 ml (18.0 mmol, 1.13 eq) of 2 N aqueous sodium hydroxide and 30 ml of dioxane was added to a white slurry of 3.97 g (20.8 mmol, 1.3 eq) of oligo (3,5-dichlorosalicylate) and 30 ml of dioxane in a 250 mL round bottom flask equipped with a magnetic stir bar and reflux condenser. The reaction mixture was heated to 90° C. for 20 hours (at which time no further change was observed, by HPLC). The reaction mixture was cooled to 25° C. and acidified to pH=1 with 2N aqueous hydrochloric acid. The mixture was concentrated in vacuo (60° C., 50 mm). The resulting solid was recrystallized twice from ethanol-water decolorized with charcoal but was not yet clean. Column chromatography using 5:1 hexanes/ethyl acetate-1% acetic acid as eluant gave one fraction as acid and another as ethyl ester. The ethyl ester was hydrolyzed to the acid using 4 ml of 2N aqueous sodium hydroxide and acidified with 2N aqueous hydrochloric acid. The acid was isolated by filtration. The combined acid portions were triturated with methylene chloride and hexanes to give 1.22 g of N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid.

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. concentrationThe mixture was concentrated in vacuo (60° C., 50 mm)
  5. customThe resulting solid was recrystallized twice from ethanol-water
  6. customgave one fraction as acid
  7. customThe acid was isolated by filtration
  8. customThe combined acid portions were triturated with methylene chloride and hexanes

Sources & evidence

ORD record
ord-79899b9921d24471ab1936a78fbcda32
Source dataset
uspto-grants-2004_02
Patent number
US06693208B2

Reaction notes

Loading…