Hydrochloric Acid → HCID 12132858, compound

HRID 22973Notes

Reaction equation

HRID 22973 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][O:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C@@H:12]1/[CH:17]=[CH:18]/[CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])C.[OH-].[Li+].Cl>CO.C1COCC1.O>[OH:25][CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])/[CH:18]=[CH:17]/[C@H:12]1[CH2:13][CH2:14][C:15](=[O:16])[N:11]1[CH2:10]/[CH:9]=[CH:8]\[CH2:7][O:6][CH2:5][C:4]([OH:26])=[O:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 12132857HCID 12132857, compound

Product 1

HCID 12132858HCID 12132858, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of {(Z)-4-[(R)-2-((E)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid ethyl ester (0.22 g, 0.6 mmol) in a mixture of 5 mL of methanol and 5 mL THF at room temperature under a nitrogen atmosphere was added an aqueous solution of lithium hydroxide (0.1 g, 2.4 mmol) in 3 mL of water. The reaction was stirred at 45° C. overnight, cooled to room temperature and treated with aqueous hydrochloric acid (1 M) until acidic. The residue was diluted with water (10 mL) and extracted with ethyl acetate. The organic solution was dried (brine, Na2SO4) and evaporated to yield {(Z)-4-[(R)-2-((E)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-but-2-enyloxy}-acetic acid; ESMS m/Z M+, 339.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solution was dried (brine, Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-9a96a1e2856a429d999ef7dab784b781
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Reaction notes

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