1,1-Dichloroethane → 2',3',5'-Tri-o-benzoyl-5-azacytidine

HRID 2369180Notes

Reaction equation

HRID 2369180 reaction equation
[NH:1]1[CH:8]=[N:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C(O[C@@H:13]1[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[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:14]1[O:15][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C.Cl[Sn](Cl)(Cl)Cl.ClC(Cl)C>>[C:16]([O:15][C@@H:14]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:34]([CH2:36][O:37][C:38](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[O:35][C@H:13]1[N:1]1[CH:8]=[N:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 24287Tin tetrachlorideHCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 178508820HCID 178508820, compound

Product 1

HCID 129072322',3',5'-Tri-o-benzoyl-5-azacytidine

Procedure

U.S. Pat. No. 3,819,780 discloses a process which involves reacting a bis-silyl compound of 5-Azacytosine with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in the presence of SnCl4 and absolute dichloroethane to give 5-azacytidine tribenzoate, which is further reacted with methanolic ammonia to give 5-azacytidine.

Sources & evidence

ORD record
ord-e99093f20a564ffe94794dec60cc66ac
Source dataset
uspto-grants-2014_04
Patent number
US08703932B2

Reaction notes

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