Hydrochloric Acid → HCID 66894995, compound

HRID 18991Notes

Reaction equation

HRID 18991 reaction equation
C([O:3][C:4](=[O:30])[CH:5]([N:15]1[CH2:19][C:18]([O:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])=[CH:17][C:16]1=[O:29])[CH2:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:8]=1[F:14])C.O.[OH-].[Li+].Cl>O1CCCC1.O>[F:28][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([F:27])[C:21]=1[O:20][C:18]1[CH2:19][N:15]([CH:5]([CH2:6][C:7]2[C:8]([F:14])=[CH:9][CH:10]=[CH:11][C:12]=2[F:13])[C:4]([OH:30])=[O:3])[C:16](=[O:29])[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66893274HCID 66893274, compound

Product 1

HCID 66894995HCID 66894995, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution containing 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(2,6-difluoro-phenyl)-propionic acid ethyl ester (96 mg, 0.23 mmol) in tetrahydrofuran (1 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (12 mg, 0.27 mmol) in water (2 mL). The mixture was stirred at 25° C. for 3 h, then acidified with 2N aqueous hydrochloric acid. The mixture was extracted with dichloromethane (2×30 mL). The combined organic layers were dried over magnesium sulfate and concentrated to afford 2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(2,6-difluoro-phenyl)-propionic acid (90 mg, 100%) as an off-white solid. LR-ES-MS m/z calculated for C19H13F4NO4 [M]+ 395, observed [M+H]+ 396.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×30 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c91bc28b15984e0b877b8f77c73e5841
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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