Methanol → 2',3'-Didehydro-3'-deoxy-4'-ethynylthymidine

HRID 1503306Notes

Reaction equation

HRID 1503306 reaction equation
C(OC([O:8][CH2:9][C@@:10]1([C:24]#[C:25][Si](C)(C)C)[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C(#N)C>[C:24]([C@:10]1([CH2:9][OH:8])[O:14][C@@H:13]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH:12]=[CH:11]1)#[CH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 53372553(2R,5R)-5-t-butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran

Product 1

HCID 30088972',3'-Didehydro-3'-deoxy-4'-ethynylthymidineYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(2R,5R)-5-t-Butoxycarbonyloxymethyl-5-(2-trimethylsilylethynyl)-2-(thymin-1-yl)-2,5-dihydrofuran (35 mg) was added to a glass reactor, and the atmosphere of the reactor was changed to nitrogen. To the reactor, potassium carbonate (72 mg) and methanol (3.5 mL) were added, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was mixed with water and acetonitrile so as to form a uniform solution, and the solution was quantitated (LC). The yielded compound was found to be 4′-ethynyl-2′,3′-didehydro-3′-deoxythymidine (yield: 94%, calculated through quantitation) (internal standard: methyl phthalate). The 1H-NMR data of the compound are as follows.

Workup

  1. customto form a uniform solution

Sources & evidence

ORD record
ord-159b293b6c044f4a8e69bf52ddaa863c
Source dataset
uspto-grants-2015_12
Patent number
US09212174B2

Reaction notes

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