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

HRID 1391715노트

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HRID 1391715 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ef76791d74da44079f4129cb09b38d69
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338974B2

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