Cyclopentanol → HCID 86679898, Verbindung

HRID 403467

Reaktionsgleichung

Reaktionsgleichung von HRID 403467
[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20](S(C)(=O)=O)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2].[CH:35]1([OH:40])[CH2:39][CH2:38][CH2:37][CH2:36]1.C(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)(C)C>>[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20]([O:40][CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 7298CyclopentanolHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Produkt 1

HCID 86679898HCID 86679898, VerbindungAusbeute 27,2 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A solution of 98 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester, 19 mg of cyclopentanol and 69 mg of (tert-butylimino)tris(pyrrolidino)phosphorane was reacted at room temperature for 16 h and subsequently heated in a microwave reactor to 100° C. for 10 min. The mixture was poured onto water and extracted twice with ethyl acetate. The combined organic layers were washed with a 10% aqueous solution of citric acid and brine, dried and evaporated. After purification by preparative HPLC, 27 mg of the title compound were obtained.

Aufarbeitung

  1. additionThe mixture was poured onto water
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with a 10% aqueous solution of citric acid and brine
  4. customdried
  5. customevaporated
  6. customAfter purification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-31c921d7ce224a1fae567d02eb829044
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748436B2

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