1192731-63-7 → HCID 67039864, compound

HRID 604534Notes

Reaction equation

HRID 604534 reaction equation
[ClH:1].O1CCOCC1.[NH2:8][C@:9]([CH3:32])([CH2:12][CH2:13][C:14]1[N:15]([CH3:31])[C:16]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[CH:17][CH:18]=1)[CH2:10][OH:11]>CO>[ClH:1].[NH2:8][C@:9]([CH3:32])([CH2:12][CH2:13][C:14]1[N:15]([CH3:31])[C:16]([C:19](=[O:30])[CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)=[CH:17][CH:18]=1)[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 113712901192731-63-7HCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 67039864HCID 67039864, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(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%).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure, ethyl acetate
  3. additionwas added
  4. filtrationthe precipitated crystal was collected by filtration
  5. washThe crystal was washed with ethyl acetate
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-58dd0689e1b44cabbe5719ba30aee07a
Source dataset
uspto-grants-2011_03
Patent number
US07910617B2

Reaction notes

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