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Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 86589094, Verbindung

HRID 1792981
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1792981
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][C:20]([OH:22])=O)[CH:9]=[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:11]=1[OH:12])[CH2:2][CH2:3][CH3:4].N[CH2:24][CH2:25][C:26]1[CH:31]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:29]([OH:36])=[C:28]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:27]=1.F[P-](F)(F)(F)(F)F.[N:48]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:52]2C=CC=C[C:51]=2N=N1>CN(C=O)C.CCN(CC)CC.C(Cl)Cl>[CH2:14]([O:13][C:10]1[CH:9]=[C:8]([CH:18]=[CH:19][C:20]([NH:48][CH2:52][CH2:51][CH2:24][CH2:25][C:26]2[CH:31]=[C:30]([C:32]([CH3:33])([CH3:34])[CH3:35])[C:29]([OH:36])=[C:28]([C:37]([CH3:39])([CH3:40])[CH3:38])[CH:27]=2)=[O:22])[CH:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:11]=1[OH:12])[CH2:15][CH2:16][CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate2×HCID 104908664-(2-Aminoethyl)-2,6-di-t-butylphenolHCID 69640036HCID 69640036, Verbindung

Produkt 1

HCID 86589094HCID 86589094, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 3-(3,5-dibutoxy-4-hydroxyphenyl) acrylic acid (53 mg, 0.17 mmol) in DMF (0.76 ml) and Et3N (39 μl), was added 4-(2-aminoethyl)-2,6-di-t-butylphenol (50 mg, 0.19 mmol) at 0° C. The obtained solution was added with the solution of benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (84 mg, 0.19 mmol) in CH2Cl2 (1 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 12 hours at room temperature. The solution was added with BOP (70 mg, 0.16 mmol) and was stirred for 1 hour. And then CH2Cl2 was evaporated in vacuo and the obtained residue was poured into ice water. The residue was extracted with EtOAc and washed with HCl (aq) and NaHCO3 (aq). And then the water was dried over anhydrous magnesium sulfate and filtered. The obtained filtrate was vacuum concentrated to give the residue, which was purified by column chromatography (EtOAc:Hexane=1:2), yielding 51 mg (91%) of the title compound as a brown oil.

Aufarbeitung

  1. stirringwas stirred for 12 hours at room temperature
  2. stirringwas stirred for 1 hour
  3. customAnd then CH2Cl2 was evaporated in vacuo
  4. additionthe obtained residue was poured into ice water
  5. extractionThe residue was extracted with EtOAc
  6. washwashed with HCl (aq) and NaHCO3 (aq)
  7. dry with materialAnd then the water was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the residue, which
  11. customwas purified by column chromatography (EtOAc:Hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-9510d77d582b450d883ef78c542b5bab
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07078407B2

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