Hydrochloric Acid → HCID 66895181, compound

HRID 19369Notes

Reaction equation

HRID 19369 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[CH:11][C:10]1=[O:22])[CH2:5][CH2:6][O:7][CH3:8].O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH2:13][N:9]([C@@H:4]([CH2:5][CH2:6][O:7][CH3:8])[C:3]([OH:23])=[O:2])[C:10](=[O:22])[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66895294(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methoxy-butyric acid methyl ester

Product 1

HCID 66895181HCID 66895181, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

In a flask was placed (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methoxy-butyric acid methyl ester (71 mg, 0.21 mmol) in tetrahydrofuran (3 mL). To this mixture at 25° C. was added a solution of lithium hydroxide monohydrate (18 mg, 0.42 mmol) in water (3 mL) and stirred for 1.5 h at 25° C. The mixture was then treated with a 1N aqueous hydrochloric acid solution to pH=2 and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methoxy-butyric acid (32 mg, 98%) as a light yellow solid.

Workup

  1. customIn a flask was placed
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e2ace90c94e4292b585c34333390a7e
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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