Propionyl chloride → 1-[2,5,6-trichloro-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]indol-3-yl]propan-1-one

HRID 28345Notes

Reaction equation

[Cl:1][C:2]1[N:3]([C@@H:13]2[O:19][C@H:18]([CH2:20][O:21]C(=O)C)[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([Cl:11])=[C:6]([Cl:12])[CH:5]=2.[C:25](Cl)(=[O:28])[CH2:26][CH3:27]>>[Cl:1][C:2]1[N:3]([C@@H:13]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:4]2[C:9]([C:10]=1[C:25](=[O:28])[CH2:26][CH3:27])=[CH:8][C:7]([Cl:11])=[C:6]([Cl:12])[CH:5]=2

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 670991842,5,6-Trichloro-1-(5-O-acetyl-beta-D-ribofuranosyl)indole

Product 1

HCID 30125781-[2,5,6-trichloro-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]indol-3-yl]propan-1-one

Procedure

The same procedure was used for the synthesis of the 3-propionyl derivative 4.47 (FIG. 6A). 2,5,6-Trichloro-1-(5-O-acetyl-β-D-ribofuranosyl)indole (4.39, FIG. 6A) was acylated under Friedel-Crafts conditions with propionyl chloride and deprotected in two steps to yield the desired 2,5,6-trichloro-3-propionyl-1-(β-D-ribofuranosyl)indole (4.47, FIG. 6A).

Sources & evidence

ORD record: ord-1deef8db739946a69e53f436f0756d25
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419963B2

Reaction notes

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