4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester → 4-(2-((R)-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl)ethylthio)butanoic acid

HRID 22970Notes

Reaction equation

HRID 22970 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CO.[OH-].[Na+]>[OH:24][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])/[CH:17]=[CH:16]/[C@H:11]1[CH2:12][CH2:13][C:14](=[O:15])[N:10]1[CH2:9][CH2:8][S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:25])=[O:2]

Participants

4

Reactant 1

HCID 121328524-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester

Product 1

HCID 98851064-(2-((R)-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl)ethylthio)butanoic acidYield 69.9%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio] butanoic acid methyl ester (0.011 g, 0.03 mmol) in 2 mL of methanol at room temperature under an argon atmosphere was added an aqueous solution of sodium hydroxide (1 M, 4-5 drops). The reaction was stirred for 4 hours, evaporated under reduced pressure 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 7.5 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid: 1H NMR (300 MHz, CDCl3) δ partial spectrum 5.74 (dd, 1H, J=5.7, 15.6 Hz), 5.53 (dd, 1 H, J=8.2, 15.6 Hz), 4.11-4.20 (m with apparent q, 2 H, J=6.0 Hz), 3.62-3.81 (m with dd, 2 H, J=2.4, 10.2 Hz), 3.08-3.20 (m, 1 H); MS m/z (M+), 357.

Workup

  1. customevaporated under reduced pressure
  2. additiontreated with aqueous hydrochloric acid (1 M) until acidic
  3. additionThe residue was diluted with water (10 mL)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic solution was dried (brine, Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-a4b9874393104e968da0ffb5624cf246
Source dataset
uspto-grants-2005_02
Patent number
US06849657B2

Reaction notes

Loading…