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

HRID 1161138Notes

Reaction equation

HRID 1161138 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-333067c38085458b871f3282395c411b
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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