Triethylamine → cis-2',3',5'-tri-O-benzoyl-2-chloro-N-(2-phenoxycyclopentyl)adenosine

HRID 1379636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379636
[O:1]([C@H:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O:22][C@@H:23]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:25][C@H:24]1[N:47]1[CH:55]=[N:54][C:53]2[C:48]1=[N:49][C:50]([Cl:57])=[N:51][C:52]=2Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCOCC1>[C:14]([O:22][C@@H:23]1[C@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:26]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:25][C@H:24]1[N:47]1[C:48]2[N:49]=[C:50]([Cl:57])[N:51]=[C:52]([NH:13][C@@H:9]3[CH2:10][CH2:11][CH2:12][C@@H:8]3[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:53]=2[N:54]=[CH:55]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 116930649-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dichloro-9H-purineHCID 30815077rac-(1R,2S)-2-phenoxycyclopentan-1-amine

Produkt 1

HCID 22877238cis-2',3',5'-tri-O-benzoyl-2-chloro-N-(2-phenoxycyclopentyl)adenosineAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

cis-2-Phenoxycyclopentylamine (0.75 g, 4.23 mmol) was combined with 9-(2,3,5-tri- O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.95 g, 4.7 mmol) and triethylamine (0.64 g, 6.3 mmol) in dioxan (30 ml) and stirred for 50 h. The reaction mixture was filtered, evaporated and the residue dissolved in ethyl acetate and washed with water (2×50 ml). The organic phase was dried (MgSO4), evaporated and the residue coevaporated to give cis-2',3',5'-tri-O-benzoyl-2-chloro- N-(2-phenoxycyclopentyl)adenosine (3.1 g, 90%) as an amorphous foam, which was deprotected using saturated methanolic ammonia (50 ml). After 70 h at room temperature the reaction mixture was evaporated and the residue purified by flash chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (19:1). The title cis-2-chloro- N-(2-phenoxycyclopentyl)adenosine (0.925 g, 53%) was obtained as an amorphous foam (a 1:1 mixture of diastereoisomers), 1H NMR (DMSO-d6)δ 1.58-2.15 (6H, 3m, --CH2CH2CH2 --), 3.51-3.60 (1 H, m, H-5'a), 3.62-3.71 (1H, m, H-5'b), 3.95 (1H, br q, H-4'), 4.12 (1H, br q, H-3'), 4.46-4.62 (2H, m, H-2' and --CH), 4.82-4.89 (1H, m, --CH), 5.07 (1H, br t, 5'-OH), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.83 (1H, d, H-1'), 6.80-6.91 (3H, m, Ar--H), 7.15-7.24 (2H, t, Ar--H), 7.99, 8.22 (1H, d & m, N--H), 8.41, 8.45 (1 H, 2s, H-8).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed with water (2×50 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f1ea27ca49c948ffa185f839c5b9280f
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05672588

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