Trifluoroacetic acid → N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

HRID 1696995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696995
C(OC(=O)[N:7]([C@H:12]1[CH2:16][C@@H:15]([N:17]2[CH:25]=[N:24][C:23]3[C:18]2=[N:19][C:20]([Cl:32])=[N:21][C:22]=3[NH:26][CH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[C@H:14]([OH:33])[C@@H:13]1[OH:34])[C:8](=[O:11])[CH2:9][CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Cl:32][C:20]1[N:19]=[C:18]2[C:23]([N:24]=[CH:25][N:17]2[C@@H:15]2[CH2:16][C@H:12]([NH:7][C:8](=[O:11])[CH2:9][CH3:10])[C@@H:13]([OH:34])[C@H:14]2[OH:33])=[C:22]([NH:26][CH:27]([CH2:28][CH3:29])[CH2:30][CH3:31])[N:21]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86622635{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester

Produkt 1

HCID 11647233N-{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

{(1S,2R,3S,4R)-4-[2-Chloro-6-(1-ethyl-propylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionyl-carbamic acid tert-butyl ester (300 mg, 0.59 mmol) is dissolved in dichloromethane (5 ml). TFA (2 ml) is added and the reaction mixture is stirred at room temperature. The reaction is shown to be complete by LCMS after 1 hour. The solvent is removed in vacuo and the residue is partitioned between dichloromethane (50 ml) and saturated NaHCO3 (50 ml). The organic layer is washed with water (20 ml) and brine (20 ml), dried over MgSO4, filtered and the solvent is removed in vacuo to give the title compound. 1H nmr (MeOD, 400 MHz); 8.05(s, 1H), 4.75(m, 1H), 4.60(m, 1H), 4.20(m, 2H), 4.00(m, 1H), 2.90(m, 1H), 2.40(q, 2H), 2.10(m, 1H), 1.70(m, 2H), 1.60(m, 2H), 1.20(t, 3H), 0.95(t, 6H), MS (ES+) mine 411 (MH+).

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between dichloromethane (50 ml) and saturated NaHCO3 (50 ml)
  3. washThe organic layer is washed with water (20 ml) and brine (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-13651a05b63d4d0db8dc129024474195
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163754B2

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