Hydrochloric Acid → HCID 58813133, compound

HRID 1391708Notes

Reaction equation

HRID 1391708 reaction equation
[Li+].[OH-].[CH2:3]([C@H:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([CH2:17][CH:18]=[CH2:19])[C:13]([O:15]C)=[O:14])[C:8]1=[O:20])[CH2:4][CH2:5][CH3:6].Cl>O.C1COCC1>[CH2:3]([C@H:7]1[CH2:11][CH2:10][N:9]([C@@H:12]([CH2:17][CH:18]=[CH2:19])[C:13]([OH:15])=[O:14])[C:8]1=[O:20])[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58813147(S)-methyl 2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate

Product 1

HCID 58813133HCID 58813133, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step B (5): A solution of LiOH (2 M, 69 mg, 2.9 mmol) in 1.4 mL of H2O was added to diastereomer A, (S)-methyl 2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoate, (242 mg, 0.96 mmol) from Step B (4) in THF (1.4 mL). The reaction mixture was stirred at room temperature for 3 days. The mixture was poured into 1 N 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 182 mg of (S)-2-((S)-3-butyl-2-oxopyrrolidin-1-yl)pent-4-enoic acid as colorless oil: LC-MS (M+H)+=240.2; 1H NMR (500 MHz, CDCl3) δ 5.60-5.82 (m, 1H), 5.03-5.21 (m, 2H), 4.74 (dd, J=10.68, 4.88 Hz, 1H), 3.38-3.48 (m, 1H), 3.29-3.38 (m, 1H), 2.70-2.81 (m, 1H), 2.51-2.62 (m, 1H), 2.36-2.49 (m, 1H), 2.11-2.25 (m, 1H), 1.79-1.91 (m, 1H), 1.66-1.79 (m, 1H), 1.23-1.43 (m, 5H), 0.80-0.96 (m, 3H).

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-3657a0cb924d470a9b43b16f46c5c621
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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