Ethyl propiolate → HCID 11962692, compound

HRID 130306Notes

Reaction equation

HRID 130306 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[C:11]#[CH:12].[CH:17]1([NH:22][C:23]2[N:31]=[C:30]([N:32]=[N+:33]=[N-:34])[N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][N:27]3[C@H:35]2[C@H:39]([OH:40])[C@H:38]([OH:41])[C@@H:37]([CH2:42][OH:43])[O:36]2)[CH2:21][CH2:20][CH2:19][CH2:18]1>C1COCC1.[Cu]I>[OH:40][C@@H:39]1[C@H:38]([OH:41])[C@@H:37]([CH2:42][OH:43])[O:36][CH:35]1[N:27]1[CH:26]=[N:25][C:24]2[C:28]1=[N:29][C:30]([N:32]1[CH:12]=[C:11]([C:10]([O:14][CH2:15][CH3:16])=[O:13])[N:34]=[N:33]1)=[N:31][C:23]=2[NH:22][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 12182Ethyl propiolateHCID 81531DiisopropylethylamineHCID 58767039HCID 58767039, compound

Product 1

HCID 11962692HCID 11962692, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.470 g of diisopropylethylamine and ethyl prop-2-ynoate (1.9 mmol) were dissolved in 20 mL of THF. To the solution was added (4S,2R,3R,5R)-2-[6-(cyclopentylamino)-2-(azido)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol (1.3 mmol) and 350 mg of CuI. The mixture was stirred at room temperature for 24 hours. The solvent was then removed by evaporation and the residue treated with 5 mL of ethanol and ethyl ether. The yellow solid was collected by filtration, and washed with ethanol and ether to afford ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}-1,2,3-triazole-4-carboxylate, a compound of Formula I.

Workup

  1. customThe solvent was then removed by evaporation
  2. additionthe residue treated with 5 mL of ethanol and ethyl ether
  3. filtrationThe yellow solid was collected by filtration
  4. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-023505bf19e648ef86caae2aed0b922e
Source dataset
uspto-grants-2008_06
Patent number
US07381714B2

Reaction notes

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