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Methanol → 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid

HRID 600552
ノート
印刷プレビュー

反応式

HRID 600552 の反応式
[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([O:19]C)=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Li+].O>C1COCC1>[N:1]1([C:5]([C:7]2[N:12]=[CH:11][C:10]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@H:25]4[CH2:29][CH2:28][N:27]([CH3:30])[C:26]4=[O:31])[CH:23]=3)[C:17]([OH:19])=[O:18])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59761163Methyl 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate2 回

生成物 1

HCID 597611453-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoic acid収率 98.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 31) (439 mg, 1.0 mmol) was dissolved in THF (6 mL) and methanol, (2 mL) and 1 N lithium hydroxide (1.24 mL) was added. Water (8 mL) was then added dropwise and the resultant solution stirred for 1 hour at room temperature. The majority of the organic solvents were removed by distillation under reduced pressure. The aqueous residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate (2×40 mL). The combined organic extracts were washed with water (10 mL) and brine (20 mL), dried (MgSO4) and evaporated under reduced pressure to afford the product (406 mg, 96%). 1H NMR δ (300 MHz, CDCl3) 2.10-2.26 (m, 2H), 2.29-2.43 (m, 2H), 2.55-2.69 (m, 1H), 2.96 (s, 3H), 3.36-3.59 (m, 4H), 4.26 (t, 2H), 4.71 (t, 2H), 4.98 (t, 1H), 6.95 (s, 1H), 7.29 (s, 3H), 7.34 (d, 2H), 7.55 (s, 1H), 8.09 (d, 1H), 8.30 (s, 1H); m/z 411 (M+H)+.

後処理

  1. customThe majority of the organic solvents were removed by distillation under reduced pressure
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. washThe combined organic extracts were washed with water (10 mL) and brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-43cecfa6902b4a7c9ae761f30d38a9eb
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07902200B2

反応ノート

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