Tetrahydrofuran → HCID 10210340, compound

HRID 1830826Notes

Reaction equation

HRID 1830826 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.[CH:30]1[C:42]2[CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34]=2[CH:33]=[CH:32][C:31]=1/[CH:43]=[CH:44]/[CH2:45]O.[CH2:47](P(CCCC)CCCC)[CH2:48][CH2:49]C.[CH2:60]1[CH2:64][O:63][CH2:62][CH2:61]1>>[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:62](=[O:63])[C:61]1[CH:60]=[CH:64][CH:49]=[CH:48][CH:47]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:45]/[CH:44]=[CH:43]/[C:31]2[CH:32]=[CH:33][C:34]3[C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:41][C:42]=3[CH:30]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 22048458HCID 22048458, compoundHCID 69513443HCID 69513443, compound

Product 1

HCID 10210340HCID 10210340, compoundYield 57%

Procedure

Under an atmosphere of nitrogen, azodicarboxylic dipiperidide (1.21 g, 6.0 mmol) was added at 0–5° C. to a stirred solution of (S)-2-(2-benzoyloxy-phenylamino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (1.13 g, 3.0 mmol), (E)-3-(9H-fluoren-2-yl)-prop-2-en-1-ol (670 mg, 3.0 mmol) and tributylphosphine (1.5 g, 6.0 mmol) in dry THF (100 ml). The mixture was stirred over night. The reaction mixture was concentrated in vacuo, 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 1.0 g (57%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-fee47de0abf64115aeae0754d9da2a1f
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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