Dichloromethane → HCID 58946310、化合物

HRID 604538ノート

反応式

HRID 604538 の反応式
C([O:4][CH2:5][C@@:6]([NH:41]C(=O)C)([CH2:39][CH3:40])[CH2:7][CH2:8][C:9]1[N:10]([CH3:38])[C:11]([C:14]([O:25]C(=O)CCCC2C=CC(C)=CC=2)=[CH:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:12][CH:13]=1)(=O)C.O.[OH-].[Li+].C(Cl)Cl>O1CCCC1.CO.O>[NH2:41][C@:6]([CH2:39][CH3:40])([CH2:7][CH2:8][C:9]1[N:10]([CH3:38])[C:11]([C:14](=[O:25])[CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:12][CH:13]=1)[CH2:5][OH:4]

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 67040326HCID 67040326、化合物

生成物 1

HCID 58946310HCID 58946310、化合物収率 93.2%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

(2R)-1-Acetoxy-2-acetylamino-2-ethyl-4-{1-methyl-5-[4-(4-methylphenyl)-1-(4-(4-methylphenyl)butanoyloxy)but-1-enyl]pyrrol-2-yl}butane (372 mg, 0.620 mmol) obtained in Example 12 (12a) was dissolved in a mixture of tetrahydrofuran (5 mL) and methanol (5 mL), and water (5 mL) and lithium hydroxide monohydrate (260 mg, 6.20 mmol) were added thereto, followed by stirring of the mixture at 50° C. for 4 hours. After cooling, water was added to the reaction mixture and methylene chloride was added thereto to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by basic silica gel (NH type) chromatography (methylene chloride:methanol, 100:1) to obtain crude (2R)-2-amino-2-ethyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol (206 mg). A 4N hydrochloric acid-dioxane solution (0.135 mL, 0.54 mmol) was added to a solution of the thus obtained crude product in methanol (5.0 mL) under ice-cooling and the mixture was stirred for 10 minutes. The mixture was concentrated under reduced pressure, ethyl acetate was added thereto and the precipitated crystal was collected by filtration. The crystal was washed with ethyl acetate and dried under reduced pressure to obtain the title compound (212 mg, yield: 88%).

後処理

  1. additionwere added
  2. temperatureAfter cooling
  3. additionwas added
  4. customto separate it
  5. customThe thus obtained organic phase was separated
  6. washwashed with a saturated aqueous NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was purified by basic silica gel (NH type) chromatography (methylene chloride:methanol, 100:1)

出典と根拠

ORDレコード
ord-121aa40fecc54cbd83b6d75dbfab1f90
出典データセット
uspto-grants-2011_03
特許番号
US07910617B2

反応ノート

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