Hydrochloric Acid → 7-Methoxynaphthalene-2-sulfonic acid [1-(1-phenoxy-isoquinolin-7-ylmethyl)-oxopyrrolidin-3-(r,s)-yl]-amide

HRID 651597

反応式

HRID 651597 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][N:22]3[CH2:26][CH2:25][C@H:24]([NH:27][S:28]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[CH:36][CH:37]=5)[CH:32]=4)(=[O:30])=[O:29])[C:23]3=[O:43])[CH:19]=2)[CH:14]=[CH:13][N:12]=1.Cl>C(Cl)Cl.O>[O:7]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][N:22]3[CH2:26][CH2:25][CH:24]([NH:27][S:28]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][C:35]([O:41][CH3:42])=[CH:36][CH:37]=5)[CH:32]=4)(=[O:29])=[O:30])[C:23]3=[O:43])[CH:19]=2)[CH:14]=[CH:13][N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 14797Potassium HydroxideHCID 155458317-Methoxy-naphthalene-2-sulfonic acid[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(s)-yl]-amide

生成物 1

HCID 120853577-Methoxynaphthalene-2-sulfonic acid [1-(1-phenoxy-isoquinolin-7-ylmethyl)-oxopyrrolidin-3-(r,s)-yl]-amide収率 83.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

Phenol (6.81 g, 72.4 mmol) and potassium hydroxide ( 0.41 g, 7.31 mmol) are added to 7-methoxynaphthalene-2-sulfonic acid [1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide (1.8 g, 3.6 mmol) and heated to 90° C. until a homogeneous mixture is obtained. The mixture is stirred overnight at 90° C., then cooled to room temperature and diluted with methylene chloride (100 mL) and water. The aqueous layer is neutralized to pH 7 using 1 N HCl, then the two layers are separated and the aqueous layer is extracted with additional methylene chloride. The combined organic layers are washed with brine, dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with a gradient of 30% EtOAc/hexanes to 60% EtOAc/hexanes to give the product (1.66 g, 3 mmol) as a white solid.

後処理

  1. customis obtained
  2. temperaturecooled to room temperature
  3. customthe two layers are separated
  4. extractionthe aqueous layer is extracted with additional methylene chloride
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography
  10. washeluting with a gradient of 30% EtOAc/hexanes to 60% EtOAc/hexanes

出典と根拠

ORDレコード
ord-e7f13aad33924752ab5db612310051c2
出典データセット
uspto-grants-2001_08
特許番号
US06281227B1

関連ノート

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