Hydrochloric Acid → HCID 58813133、化合物

HRID 1391708ノート

反応式

HRID 1391708 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 58813133HCID 58813133、化合物収率 79.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

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-3657a0cb924d470a9b43b16f46c5c621
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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