Dichloromethane → 1192731-63-7

HRID 604533노트

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HRID 604533 반응식
C([O:4][CH2:5][C@@:6]([NH:40]C(=O)C)([CH3:39])[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>[NH2:40][C@:6]([CH3:39])([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]

참가 물질

7

반응물 3

HCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 67040558HCID 67040558, 화합물

생성물 1

HCID 113712901192731-63-7수율 83.3%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

(2R)-1-Acetoxy-2-acetylamino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)-1-(4-(4-methylphenyl)butanoyloxy)but-1-enyl]pyrrol-2-yl}butane (5.15 g,8.80 mmol) obtained in Example 1 (1a) was dissolved in a mixture of tetrahydrofuran (52 mL) and methanol (52 mL), and water (52 mL) and lithium hydroxide monohydrate (3.68 g, 87.7 mmol) were added thereto, followed by stirring of the mixture at 50° C. for 4 hours. After cooling, water and methylene chloride were added to the reaction mixture to separate it. The thus obtained organic phase was separated, washed with a saturated aqueous NaCl solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel (NH type) chromatography (methylene chloride:metahanol, 100:1) to obtain (2R)-2-amino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol (2.51 g). A 4N hydrochloric acid-dioxane solution (0.42 mL, 1.68 mmol) was added to a solution of the thus obtained (2R)-2-amino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol (600 mg, 1.80 mmol) in methanol (9 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 (500 mg, yield: 86%).

후처리

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

출처 및 근거

ORD 기록
ord-8a036f32e73545b6b196da244928e8dc
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910617B2

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