Benzoyl chloride → N-Benzoyl-2'-O-(2-methoxyethyl)adenosine

HRID 1168586Notes

Reaction equation

HRID 1168586 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[O:24][C@@H:23]([N:25]2[C:34]3[N:33]=[CH:32][N:31]=[C:29]([NH2:30])[C:28]=3[N:27]=[CH:26]2)[C@H:22]([O:35][CH2:36][CH2:37][O:38][CH3:39])[C@@H:21]1[OH:40])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:59](Cl)(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[C:59]([NH:30][C:29]1[C:28]2[N:27]=[CH:26][N:25]([C:34]=2[N:33]=[CH:32][N:31]=1)[C@@H:23]1[O:24][C@H:20]([CH2:19][OH:18])[C@@H:21]([OH:40])[C@H:22]1[O:35][CH2:36][CH2:37][O:38][CH3:39])(=[O:66])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

4

Reactant 3

HCID 7412Benzoyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 21348484HCID 21348484, compound

Product 1

HCID 21348490N-Benzoyl-2'-O-(2-methoxyethyl)adenosine

Procedure

5′-O-t-Butyldiphenylsilyl-2′-O-(methoxyethyl)adenosine is treated with TBAF as per the procedure of Example 8 and subsequently treated with benzoyl chloride as per the procedure of Example 4 to give the title compound.

Sources & evidence

ORD record
ord-f966a965390c4ed9a4159614ea5b2f34
Source dataset
uspto-grants-2003_09
Patent number
US06624294B2

Reaction notes

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