Hydrochloric Acid → 9-((1R,4S)-4-Ethoxycarbonyloxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

HRID 215885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 215885
[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([OH:19])[CH:16]=[CH:15]2)=[C:7]([NH:20][C@H:21]([CH2:29][OH:30])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:6]=1)=[O:4].N1C=CC=CC=1.Cl[C:38]([O:40][CH2:41][CH3:42])=[O:39].Cl>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([O:19][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:16]=[CH:15]2)=[C:7]([NH:20][C@H:21]([CH2:29][OH:30])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:6]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 670229569-((1R,4S)-4-Hydroxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

Produkt 1

HCID 670229929-((1R,4S)-4-Ethoxycarbonyloxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

9-((1R,4S)-4-Hydroxy-cyclopent-2-enyl)-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (Intermediate WA) is dissolved in THF (dry). Pyridine is added and the reaction mixture is cooled to 0° C. Ethyl chloroformate is added dropwise keeping the temperature below 10° C. The reaction mixture is warmed to RT and stirred for 2 hours. The reaction mixture is reduced in vacuo and portioned between EtOAc and (1 M) HCl(aq). The organics are washed with water, brine, dried (MgSO4) and reduced in vacuo. The resulting residue is columned to give the title compound.

Aufarbeitung

  1. customthe temperature below 10° C
  2. temperatureThe reaction mixture is warmed to RT
  3. washThe organics are washed with water, brine
  4. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-2e23cfc3ddc04694b21652596109c85c
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193164B2

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