Ammonium Hydroxide → Cdc-801

HRID 2348

Reaktionsgleichung

Reaktionsgleichung von HRID 2348
[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.C(N1C=CN=C1)([N:33]1C=CN=C1)=O.[OH-].[NH4+]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C:8]([NH2:33])=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12

Komponenten

6

Edukt 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 98016133-(3-Cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid

Produkt 1

HCID 9844338Cdc-801Ausbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 3-phthalimido-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid (2.05 g, 5.00 mmol), 1,1'-carbonyldiimidazole (0.91 g, 5.5 mmol) and 4-dimethylaminopyridine (trace) in tetrahydrofuran (20 mL) was stirred for 1.5 hours under nitrogen at approximately 25° C. To the solution was added ammonium hydroxide (1.07 mL, 16.0 mmol, 28-30%) and stirring was continued for 1.5 hours. A small amount of solid forms during this time. The mixture was concentrated to half its volume and a white solid precipitated. The mixture was filtered, washed with a small amount of tetrahydrofuran, air dried, and dried in vacuo (60° C.,<1 mm) to afford 1.27 g of the product. The product was further purified by flash column chromatography (silica gel, 5% methanol/methylene chloride) and the resulting white solid was dried in vacuo (60° C., <1 mm) to afford 1 g (49%) of the product: mp 165°-166° C.; 1H NMR (CDCl3) δ 7.85-7.61 (m, 4H), 7.16-7.04 (m, 2H), 6.85-6.75 (m, 1H), 5.80 (dd, J=5.8, 10.4 Hz, 1H), 5.66 (br s, 1H), 5.54 (br s, 1H), 4.82-4.70 (m, 1H), 3.80 (s, 3H), 3.71 (dd, J=10.4, 15 Hz, 1H), 3.06 (dd, J=5.8, 15 Hz, 1H), 2.06-1.51 (m, 8H); 13C NMR (CDCl3) δ 171.8, 168.3, 149.8, 147.7, 133.9, 131.8, 131.3, 123.3, 119.9, 114.6, 111.8, 80.4, 56.0, 51.6, 37.9, 32.7, 24.1; Anal. Calcd for C23 H24N2O5. Theoretical: C, 67.63; H, 5.92; N, 6.86. Found: C, 67.25; H, 5.76; N, 6.68.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1.5 hours
  3. concentrationThe mixture was concentrated to half its volume
  4. customa white solid precipitated
  5. filtrationThe mixture was filtered
  6. washwashed with a small amount of tetrahydrofuran, air
  7. customdried
  8. customdried in vacuo (60° C.,<1 mm)

Quellen und Nachweise

ORD-Eintrag
ord-f310c91312a24ed185ed64c535694b9b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728844

Verknüpfte Notizen

Wird geladen…