Acetic Acid → HCID 11728884, compound

HRID 1589895Notes

Reaction equation

[C:1](Br)(=[O:3])[CH3:2].[BrH:5].[C:6]([OH:9])(=[O:8])[CH3:7].[C@@H:10]1([N:19]2[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]2=[O:21])[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13](O)[C@H:11]1O>>[C:6]([O:9][C@@H:13]1[C@@H:15]([CH2:16][O:17][C:1](=[O:3])[CH3:2])[O:18][C@@H:10]([N:19]2[CH:26]=[CH:25][C:23](=[O:24])[NH:22][C:20]2=[O:21])[C@@H:11]1[Br:5])(=[O:8])[CH3:7]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 260Hydrogen Bromide

HCID 6029Uridine

HCID 10482Acetyl bromide

Product 1

HCID 11728884HCID 11728884, compound

Procedure

For example, addition of excess acetyl bromide (3.2 eq) plus 30% HBr in acetic acid (1.2 eq) to uridine at 55°-60° C. gave the desired 3',5'-di-O-acetyl-2'-bromo-2'-deoxyuridine 2 (FIG. 1; X=O in uridine and uridine derivatives) in excellent yield (>95%). 3',4'-Di-O-acetyl-2'-bromo-2'-deoxyuridine 2 was then reduced to 3 by tributyltin hydride (provided either as the premade compound or prepared by in situ generation through the reaction of tributyltin chloride with sodium borohydride) in absolute ethanol in excellent yield (>95%). 2',3'-Di-O-acetyl-2'-deoxyuridine was treated with methanolic ammonia to obtain an excellent yield of 2'-deoxyuridine. The overall yield of this process was 72-76% without chromatography.

Workup

customat 55°-60° C.

Sources & evidence

ORD record: ord-15039e20bef349d8960b3630a585b81f
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200514

Reaction notes

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