Triphenylphosphine → K-604

HRID 2103965노트

반응식

HRID 2103965 반응식
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][S:14][C:15]1[C:20]([NH:21][C:22](=[O:25])[CH2:23]O)=[C:19]([S:26][CH3:27])[CH:18]=[C:17]([CH3:28])[N:16]=1.[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[NH:31][C:30]=1[S:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.O>[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[NH:31][C:30]=1[S:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][N:44]([CH2:23][C:22]([NH:21][C:20]2[C:15]([S:14][CH3:13])=[N:16][C:17]([CH3:28])=[CH:18][C:19]=2[S:26][CH3:27])=[O:25])[CH2:43][CH2:42]1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99617871-[2-(Benzimidazol-2-ylthio)ethyl]piperazineHCID 69064831N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]-2-hydroxyacetamide

생성물 1

HCID 9892288K-604수율 51.4%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

실험 절차

Diethyl azodicarboxylate (1.88 mL, 4.33 mmol) was added dropwise to a solution of N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]-2-hydroxyacetamide (373 mg, 1.44 mmol), 1-[2-(benzimidazol-2-ylthio)ethyl]piperazine (1.40 g, 5.34 mmol), and triphenylphosphine (1.34 g, 5.09 mmol) in dimethylformamide (DMF) (20 mL) under stirring with water cooling over 5 minutes. The resultant mixture was stirred at room temperature for 60 minutes, and water (2 mL) was added thereto so as to deactivate the reagent. The reaction mixture was partitioned between 1N hydrochloric acid (30 mL) and ethyl acetate (30 mL). The formed organic layer was extracted with 1N hydrochloric acid (15 mL×2). The formed aqueous layers were combined, and the thus-combined aqueous layer was washed with ethyl acetate (20 mL×2). The pH of the resultant mixture was adjusted to 8 to 9 with 1N sodium hydroxide. The formed aqueous layer was extracted with ethyl acetate (20 mL×3). The organic layer was washed with saturated brine, and dried over sodium sulfate anhydrate, followed by solvent removal under reduced pressure. The residue was purified through silica gel column chromatography (developer: chloroform:methanol=100:3). The obtained oily substances were crystallyzed from ethanol and ether, to thereby yield 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide as colorless crystals (372 mg, yield: 51%).

후처리

  1. customThe reaction mixture was partitioned between 1N hydrochloric acid (30 mL) and ethyl acetate (30 mL)
  2. extractionThe formed organic layer was extracted with 1N hydrochloric acid (15 mL×2)
  3. washthe thus-combined aqueous layer was washed with ethyl acetate (20 mL×2)
  4. extractionThe formed aqueous layer was extracted with ethyl acetate (20 mL×3)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydrate
  7. customfollowed by solvent removal under reduced pressure
  8. customThe residue was purified through silica gel column chromatography (developer: chloroform:methanol=100:3)

출처 및 근거

ORD 기록
ord-e36e9c47b0484293b5ae209c193b058d
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576203B2

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