Triphenylphosphine → HCID 86649449, compound

HRID 2037359Notes

Reaction equation

HRID 2037359 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([CH3:24])[N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[OH:26])[CH3:2].[CH2:27]1[O:29][C@@H:28]1[CH2:30]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=[C:16]([CH3:24])[N:15]=3)[O:11][N:10]=2)[CH:6]=[C:5]([CH3:25])[C:4]=1[O:26][CH2:30][C@@H:28]1[CH2:27][O:29]1)[CH3:2]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 5460455(+)-Glycidol2×HCID 5462977Diethyl azodicarboxylate2×HCID 136344049HCID 136344049, compound

Product 1

HCID 86649449HCID 86649449, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-ethyl-4-[5-(4-isobutyl-6-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenol (79 mg, 0.224 mmol) in THF (6 mL), (R)-(+)-glycidol (25 mg, 0.335 mmol) and triphenyl phosphine (88 mg, 0.335 mmol) are added. The mixture is stirred and cooled to 0° C. before DEAD (58 mg, 0.335 mmol, as a 40% solution in toluene) is added. The mixture is warmed to rt and stirring is continued for 4 h. Another portion of (R)-(+)-glycidol (8 mg, 0.112 mmol), triphenyl phosphine (30 mg, 0.112 mmol) and DEAD (19 mg, 0.112 mmol) is added. Stirring is continued for 4 h before the solvent is evaporated. The crude product is purified on prep. TLC using heptane:EA 7:3 to give 2-[3-((S)-3-ethyl-5-methyl-4-oxiranylmethoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-4-isobutyl-6-methyl-pyridine (46 mg) as a yellow oil; LC-MS: tR=1.17 min, [M+H]+=408.19.

Workup

  1. stirringstirring
  2. stirringStirring
  3. waitis continued for 4 h before the solvent
  4. customis evaporated
  5. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-6c941b7cc20a468bbd2db9559ee0c904
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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