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Triethylamine → acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl ester

HRID 2262628
ノート
印刷プレビュー

反応式

HRID 2262628 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:32]([O:35][CH2:36][CH2:37][CH2:38]Br)(=[O:34])[CH3:33]>CN(C)C=O.[I-].[Na+]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:38][CH2:37][CH2:36][O:35][C:32](=[O:34])[CH3:33])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]
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 3

HCID 8471TriethylamineHCID 122357751-Propanol, 3-bromo-, 1-acetateHCID 574700744-Isopropyl-N-((S)-4-pyrrolidin-3-yl-phenyl)-benzenesulfonamide

生成物 1

HCID 53628668acetic acid 3-{(S)-3-[4-(4-isopropyl-benzenesulfonylamino)-phenyl]-pyrrolidin-1-yl}-propyl ester収率 94.3%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide
触媒
HCID 6228Dimethylformamide溶媒

実験手順

0.21 g of 4-isopropyl-N-[4-((S)-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.62 mmol) were dissolved in 5 ml dimethylformamide. 0.0019 mg of sodium iodide (0.01 mmol) and 0.13 ml of triethylamine (0.94 mmol) were added, followed by addition of 0.136 mg of 3-acetoxy-1-bromo-propane (0.75 mmol). Stirring continued for 15 h at room temperature before the reaction mixture was poured onto 50 ml of crushed ice. The aqueous layer was extracted three times with ethyl acetate and the combined organic phases washed with water and saturated sodium chloride solution. The ethyl acetate phase was dried over magnesium sulfate, filtered, and evaporated to dryness under reduced pressure to yield 0.26 g of the crude product.

後処理

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washthe combined organic phases washed with water and saturated sodium chloride solution
  3. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-7f477556e16d4454bf0c24ff8840e1af
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07851463B2

反応ノート

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