Triphenylphosphine → Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamate

HRID 49376

Reaktionsgleichung

Reaktionsgleichung von HRID 49376
[C:1]1([C:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1.O1CCCC1>[CH2:44]([O:43][C:42](=[O:51])[NH:41][CH2:40][CH2:39][O:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[S:10][CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[CH:17][CH:16]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 280458benzyl N-(2-hydroxyethyl)carbamateHCID 1356483144-(4-Phenyl-1,3-thiazol-2-yl)phenol

Produkt 1

HCID 12071998Benzyl-{2-[4-(4-phenyl-thiazol-2-yl)-phenoxy]-ethyl}-carbamateAusbeute 45,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-(4-Phenyl-thiazol-2-yl)-phenol (516 mg, 2.03 mmol) was dissolved in toluene (6.8 ml), and triphenylphosphine (786 mg, 3.00 mmol) and benzyl N-(2-hydroxyethyl)-carbamate (585 mg, 3.00 mmol) were added. The solution was cooled to about 0° C. and 1,1-(azodicarbonyl)-dipiperidine (757 mg, 3.00 mmol) was added. The mixture was allowed to stir for about 10 minutes at about 0° C. and was then allowed to warm to room temperature. An additional 6.8 ml of toluene and 6.8 ml of tetrahydrofuran were added to the viscous solution. The reaction mixture was stirred for about forty-eight hours, and then the solids were filtered off and rinsed with a minimum volume of 1:1 toluene/tetrahydrofuran. The filtrate was concentrated in vacuo to a semisolid which was then purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride) to give 396 mg of pure product (45% yield). LRMS ([M+H]+)=430.9.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringThe reaction mixture was stirred for about forty-eight hours
  3. filtrationthe solids were filtered off
  4. washrinsed with a minimum volume of 1:1 toluene/tetrahydrofuran
  5. concentrationThe filtrate was concentrated in vacuo to a semisolid which
  6. customwas then purified by column chromatography (silica gel; methylene chloride to 2% methanol/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-5fa7e2edfe1d42a091f266ad74be7784
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706743B2

Verknüpfte Notizen

Wird geladen…