Tetrahydrofuran → HCID 9937897, compound

HRID 1830823Notes

Reaction equation

HRID 1830823 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1OC(=O)C1C=CC=CC=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:30]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:35]=[CH:34][C:33](/[CH:36]=[CH:37]/[CH2:38]O)=[CH:32][CH:31]=1.[CH2:46](P(CCCC)CCCC)[CH2:47][CH2:48]C.[CH2:59]1[CH2:63][O:62][CH2:61][CH2:60]1>O>[CH3:1][O:2][C:3](=[O:29])[C@@H:4]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:61](=[O:62])[C:60]1[CH:59]=[CH:63][CH:48]=[CH:47][CH:46]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:38]/[CH:37]=[CH:36]/[C:33]2[CH:34]=[CH:35][C:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:31][CH:32]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 13897924(2E)-3-[1,1′-Biphenyl]-4-yl-2-propen-1-olHCID 69513443HCID 69513443, compound

Product 1

HCID 9937897HCID 9937897, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an atmosphere of nitrogen, azodicarboxylic dipiperidide (620 mg, 2.5 mmol) was added at 0–5° C. to a stirred solution of (S)-2-(2-benzoyloxy-phenylamino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (470 mg, 1.25 mmol), (E)-3-(4-biphenylyl)-2-propen-1-ol (260 mg, 1.25 mmol) and tributylphosphine (500 mg, 2.5 mmol) in dry THF (50 ml). The mixture was stirred over night. The reaction mixture was diluted with water and the product extracted with ethyl acetate. The organic layers were combined, washed with water, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (eluent: 25% ethyl acetate in heptane) to give 420 mg (60%) of the title compound.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was then purified by column chromatography on silica (eluent: 25% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-7e65e3d60b3b4be98721bbd32fa6f217
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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