Hydrochloric Acid → HCID 66884391, compound

HRID 1582218Notes

Reaction equation

HRID 1582218 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:30])[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@H:13]1[CH2:18][CH2:19][CH:20]([OH:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1.Cl>C1COCC1>[Cl:28][C:24]1[CH:23]=[C:22]([CH2:21][CH:20]([OH:29])[CH2:19][CH2:18][C@@H:13]2[CH2:14][CH2:15][C:16](=[O:17])[N:12]2[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][C:5]([OH:30])=[O:4])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66884852HCID 66884852, compound

Product 1

HCID 66884391HCID 66884391, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous lithium hydroxide (1.0 N, 0.04 mL) was added to a solution of (4-{(R)-2-[4-(3-chlorophenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (15 mg, 0.036 mmol) in THF (0.5 mL) at rt. After 1 h, aqueous HCl (1.0 N, 3 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (0%→3% MeOH/CH2Cl2) to afford 6.3 mg (43%) of (4-{(R)-2-[4-(3-chlorophenyl)-3-hydroxy-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (0%→3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2dd04839f2c04571b4fd9ffe99f5fa8c
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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