Hydrochloric Acid → Firategrast

HRID 1454110Notes

Reaction equation

HRID 1454110 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:5]=1[C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([O:28][CH3:29])=[CH:26][C:25]([CH2:30][O:31][CH2:32][CH3:33])=[CH:24][C:23]=2[O:34][CH3:35])=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11])=[O:7].Cl>O.O1CCCC1>[F:3][C:4]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:5]=1[C:6]([NH:8][C@@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]([O:34][CH3:35])=[CH:24][C:25]([CH2:30][O:31][CH2:32][CH3:33])=[CH:26][C:27]=2[O:28][CH3:29])=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11237832HCID 11237832, compound

Product 1

HCID 9935681FirategrastYield 96%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of sodium hydroxide (2.9 g) in water-tetrahydrofuran (317 ml-159 ml) was added ethyl (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (31.7 g) at 15° C. and the mixture was stirred for 4 hours at the same temperature. After neutralizing with 1N HCl, the organic solvent was removed in vacuo. 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 (28.8 g).

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-05dc434d64d34e8fb0320530f58f5fc2
Source dataset
uspto-grants-2009_01
Patent number
US07476758B2

Reaction notes

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