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

HRID 1391715ノート

反応式

HRID 1391715 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ef76791d74da44079f4129cb09b38d69
出典データセット
uspto-grants-2008_03
特許番号
US07338974B2

反応ノート

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