Tetrahydrofuran → HCID 10143680, compound

HRID 1830832Notes

Reaction equation

HRID 1830832 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.[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1/[CH:40]=[CH:41]/[CH2:42]O.[CH2:44](P(CCCC)CCCC)[CH2:45][CH2:46]C.[CH2:57]1[CH2:61][O:60][CH2:59][CH2:58]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:59](=[O:60])[C:58]1[CH:57]=[CH:61][CH:46]=[CH:45][CH:44]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:42]/[CH:41]=[CH:40]/[C:31]2[CH:32]=[CH:33][C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:30]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 6479255HCID 6479255, compoundHCID 69513443HCID 69513443, compound

Product 1

HCID 10143680HCID 10143680, compound

Procedure

Under an atmosphere of nitrogen, azodicarboxylic dipiperidide (504 mg, 2.0 mmol) was added at 0–5° C. to a stirred solution of (S)-2-(2-benzoyloxy-phenylamino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (300 mg, 0.8 mmol), (E)-3-quinolin-2-yl-prop-2-en-1-ol (185 mg, 1.0 mmol) and tributylphosphine (404 mg, 2.0 mmol) in dry THF (30 ml). The mixture was stirred for 1.5 h. 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 purified by column chromatography on a CN-column, eluting with acetonitrile+0.1% TFA graduated with from 20–100% water+0.1% TFA. The title compound was isolated in 100 mg yield.

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 purified by column chromatography on a CN-column
  8. washeluting with acetonitrile+0.1% TFA

Sources & evidence

ORD record
ord-7107f101d1e742a4b12c7f9cacb20002
Source dataset
uspto-grants-2006_06
Patent number
US07067530B2

Reaction notes

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