Acetic Acid → HCID 68380776, compound

HRID 595454Notes

Reaction equation

[CH3:1][C@@:2]1([OH:18])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].[C:19]([OH:22])(=O)[CH3:20]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:3]([O:18][C@:2]1([CH3:1])[C@H:6]([O:7][C:6](=[O:7])[CH3:5])[C@@H:5]([CH2:8][O:9][C:19](=[O:22])[CH3:20])[O:4][C@H:3]1[N:10]1[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]1=[O:12])(=[O:4])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The preparation of Compound 55 is illustrated in Scheme 5, above. To a solution of 2′-C-methyluridine (1 g) in pyridine (40 ml) were added acetic acid (3 ml) and DMAP. The mixture was stirred at 50° C. during 3 hours, followed by two days at room temperature. Then, the mixture was concentrated and co-evaporated with toluene and the residue purified by silica gel chromatography eluting with 0→10% methanol in dichloromethane to yield 2′,3′,5′-Tri-O-acetyl-2′-C-methyluridine (93%). MS (ESI, EI+) m/z=385.2 (MH+).

Workup

waitfollowed by two days at room temperature
concentrationThen, the mixture was concentrated and co-evaporated with toluene
customthe residue purified by silica gel chromatography
washeluting with 0→10% methanol in dichloromethane

Sources & evidence

ORD record: ord-002641dc01614c8bb3520323e0095669
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243025B2

Reaction notes

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