Triethylamine → 2',3',5'-tri-O-benzoyl-2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl]adenosine

HRID 375145Notes

Reaction equation

[C:1]([O:9][C@@H:10]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:24][O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:12][C@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][C:37]([Cl:44])=[N:38][C:39]=2Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.NC(C)C[C@H:50]([S:53][C:54]1[S:55][CH:56]=[CH:57][N:58]=1)[CH2:51][CH3:52].C([N:62](CC)CC)C>O1CCOCC1>[C:1]([O:9][C@@H:10]1[C@H:24]([O:25][C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:13]([CH2:14][O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@H:11]1[N:34]1[C:35]2[N:36]=[C:37]([Cl:44])[N:38]=[C:39]([NH:62][C@H:51]([CH3:52])[CH2:50][S:53][C:54]3[S:55][CH:56]=[CH:57][N:58]=3)[C:40]=2[N:41]=[CH:42]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.5 g, 2.4 mmol) in dry dioxan (50 ml), the above 2-[(R)-2-aminopropyl-1-propylthio]thiazole dihydrochloride (1.5 g, 7.1 mmol) and triethylamine (0.78 g, 7.7 mmol) were introduced at 20° C. After stirring at 50° C. for 40 h the reaction mixture was concentrated to a yellow oil, which was purified by flash chromatography eluting with a mixture of heptane and ethyl acetate (1:1), to afford the title 2',3',5'-tri-O-benzoyl-2-chloro-N-[(R)-1-(2-thiazolyl)thio-2-propyl]adenosine (1.2 g, 63%) as a foam, TLC Rf 0.19 [SiO2 ; heptane/ethyl acetate (1:1)].

Workup

concentrationwas concentrated to a yellow oil, which
customwas purified by flash chromatography
washeluting with a mixture of heptane and ethyl acetate (1:1)

Sources & evidence

ORD record: ord-0aeab7268abb439da4b6d0992152a8e0
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484774

Reaction notes

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