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Triphenylphosphine → 4-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester

HRID 1161138
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HRID 1161138 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:20]([O:22][C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[O:35][N:34]=[C:33]([CH2:36][OH:37])[N:32]=2)=[CH:26][CH:25]=1)[CH3:21].[Cl:39][C:40]1[C:41]([OH:50])=[C:42]([C:47](=[O:49])[CH3:48])[CH:43]=[CH:44][C:45]=1O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH2:20]([O:22][C:23](=[O:38])[C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]2[O:35][N:34]=[C:33]([CH2:36][O:37][C:45]3[CH:44]=[CH:43][C:42]([C:47](=[O:49])[CH3:48])=[C:41]([OH:50])[C:40]=3[Cl:39])[N:32]=2)=[CH:28][CH:29]=1)[CH3:21]
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참가 물질

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반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 574382941-(3-Chloro-2,4-dihydroxy-phenyl)ethanoneHCID 666995924-(3-Hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl ester

생성물 1

HCID 666995484-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Add polymer support PPh3 (287 mg, 0.86 mmol to a solution of 4-(3-hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl ester (80 mg, 0.41 mmol) in anhydrous CH2Cl2 (8 mL) under argon gas at room temperature. Add 1-(3-chloro-2,4-dihydroxy-phenyl)-ethanone (115 mg, 0.62 mmol) to the mixture, followed by diisopropyl azodicarboxylate (194 μL, 0.86 mmol). After 1.5 hours at room temperature, remove the polymer by filtration and concentrate the filtrate. Purify the residue by flash column chromatography using 30% ethyl acetate/hexane to give the title compound (60 mg, 34%). LC-MS (m/e): 429 (M−1).

후처리

  1. customremove the polymer
  2. filtrationby filtration
  3. concentrationconcentrate the filtrate
  4. customPurify the residue by flash column chromatography

출처 및 근거

ORD 기록
ord-333067c38085458b871f3282395c411b
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816523B2

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