Hydrochloric Acid → Firategrast

HRID 1454112Notes

Reaction equation

HRID 1454112 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:25]([O:26][CH3:27])=[CH:24][C:23]([CH2:28][O:29][CH2:30][CH3:31])=[CH:22][C:21]=2[O:32][CH3:33])=[CH:16][CH:15]=1)[C:8]([O:10]CC)=[O:9])=[O:5].Cl>O.O1CCOCC1>[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:3]=1[C:4]([NH:6][C@@H:7]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:21]([O:32][CH3:33])=[CH:22][C:23]([CH2:28][O:29][CH2:30][CH3:31])=[CH:24][C:25]=2[O:26][CH3:27])=[CH:18][CH:19]=1)[C:8]([OH:10])=[O:9])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11237832HCID 11237832, compound

Product 1

HCID 9935681FirategrastYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (500 mg) in water (12.6 ml) and dioxane (50 ml) was added hydrochloric acid (12.4 g) and the mixture was stirred for 60 hours at 60° C. The organic solvent was removed in vacuo and the aqueous layer was cooled. The crystalline precipitates were collected by filtration and recrystallized from ethanol-water to yield (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionic acid (426 mg). The physicochemical data were the same as that obtained in Example 1.

Workup

  1. customThe organic solvent was removed in vacuo
  2. temperaturethe aqueous layer was cooled
  3. customThe crystalline precipitates
  4. filtrationwere collected by filtration
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-87be99053b094cac8fd986cbd9be5ba4
Source dataset
uspto-grants-2009_01
Patent number
US07476758B2

Reaction notes

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