Hydrochloric Acid → HCID 66884698, compound

HRID 1582220Notes

Reaction equation

HRID 1582220 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/[CH:18]=[CH: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])/[CH:19]=[CH: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 66884695HCID 66884695, compound

Product 1

HCID 66884698HCID 66884698, compoundYield 97.2%

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-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (16 mg, 0.039 mmol) in THF (0.25 mL) at rt. After 1 h, aqueous HCl (0.5 N, 3 mL) was added and the mixture was extracted with ETOAc (2×5 mL). The combined organic phase was washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 15 mg (97%) of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-hydroxy-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid.

Workup

  1. extractionthe mixture was extracted with ETOAc (2×5 mL)
  2. washThe combined organic phase was washed with brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a14709ea49f4d929a8c8e8abc107771
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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