Hydrochloric Acid → (S)-2-((S)-3-isobutyl-2-oxopyrrolidin-1-yl)pent-4-enoic acid

HRID 1391715Notes

Reaction equation

HRID 1391715 reaction equation
[Li+].[OH-].O.[CH2:4]([C@H:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([O:16]C)=[O:15])[C:9]1=[O:21])[CH:5]([CH3:7])[CH3:6].Cl>C1COCC1>[CH2:4]([C@H:8]1[CH2:12][CH2:11][N:10]([C@@H:13]([CH2:18][CH:19]=[CH2:20])[C:14]([OH:16])=[O:15])[C:9]1=[O:21])[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58813107(S)-methyl 2-((S)-3-isobutyl-2-oxopyrrolidin-1-yl)pent-4-enoate

Product 1

HCID 58813136(S)-2-((S)-3-isobutyl-2-oxopyrrolidin-1-yl)pent-4-enoic acidYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step M (5): A solution of LiOH/H2O (2M, 40 mg in 1.0 mL) was added to the diastereomer A, (S)-methyl 2-((S)-3-isobutyl-2-oxopyrrolidin-1-yl)pent-4-enoate (138 mg, 0.55 mmol) from Step M (4) in THF (1.0 mL) at RT. The reaction was stirred for 3 days. The mixture was poured into 1N HCl and the aqueous layer was extracted with EtOAC. The combined organic layers were washed with brine, dried over NaSO4 and concentrated in vacuo to give 88 mg (67%) of the title compound as white solid: LC-MS (M+H)+=240.04. 1H NMR (300 MHz, CDCl3) δ ppm 0.82-0.95 (m, 7H) 1.16-1.30 (m, 1H) 1.59-1.79 (m, 3H) 2.09-2.26 (m, 1H) 2.39-2.60 (m, 2H) 2.68-2.80 (m, 1H) 3.24-3.48 (m, 2H) 4.67-4.76 (m, 1H) 5.01-5.20 (m, 2H) 5.60-5.79 (m, 1H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAC
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over NaSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef76791d74da44079f4129cb09b38d69
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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