Acetoxyacetyl chloride → Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

HRID 1929771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929771
Cl.Cl.[NH2:3][C@H:4]1[CH2:8][C@@H:7]([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][C:12]([Cl:33])=[N:13][C:14]=3[NH:18][CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:6]([OH:34])[C@@H:5]1[OH:35].[C:36]([O:39][CH2:40][C:41](Cl)=[O:42])(=[O:38])[CH3:37]>C1COCC1>[Cl:33][C:12]1[N:11]=[C:10]2[C:15]([N:16]=[CH:17][N:9]2[C@@H:7]2[CH2:8][C@H:4]([NH:3][C:41]([CH2:40][O:39][C:36](=[O:38])[CH3:37])=[O:42])[C@@H:5]([OH:35])[C@H:6]2[OH:34])=[C:14]([NH:18][CH2:19][CH:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:13]=1

Komponenten

4

Edukt 2

HCID 26297Acetoxyacetyl chlorideHCID 86637574(1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol dihydrochloride

Produkt 1

HCID 86637573Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of (1S,2R,3S,5R)-3-amino-5-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-cyclopentane-1,2-diol dihydrochloride (Intermediate AAI13) (250 mg, 0.46 mmol) in dry THF (10 mL) is treated with TEA (0.188 g, 1.86 mmol) followed by acetoxyacetylchloride (0.064 g, 0.46 mmol) and then stirred at room temperature for 30 minutes. The solvent is removed in vacuo and the solvent is partitioned between DCM and 0.1 M HCl. The organic portion is separated and washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title product. MS (ES+) m/e 565.38 (MH+).

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe solvent is partitioned between DCM and 0.1 M HCl
  3. customThe organic portion is separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e5fb4b62a53e4ee4a6b19c882b9a055c
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188100B2

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