Dimethyl oxalate → HCID 178501825, compound

HRID 1297144Notes

Reaction equation

HRID 1297144 reaction equation
CC(C)([O-])C.[Na+].[C:7]([O:13][CH3:14])(=[O:12])[C:8]([O:10]C)=O.[C:15]([C:18]1[C:19](=[O:39])[N:20]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21](=[O:31])[N:22]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=1)(=[O:17])[CH3:16]>C1COCC1>[CH2:24]([N:22]1[CH:23]=[C:18]([C:15](=[O:17])[CH:16]=[C:8]([OH:10])[C:7]([O:13][CH3:14])=[O:12])[C:19](=[O:39])[N:20]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]1=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11120Dimethyl oxalateHCID 116744085-Acetyl-1,3-dibenzyluracilHCID 23676156Sodium t-butoxide

Product 1

HCID 178501825HCID 178501825, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of sodium t-butoxide (577 mg, 6 mmol) in anhydrous THF (15 ml) at room temperature was added, dropwise, dimethyl oxalate (472 mg, 4 mmol) in THF (7 ml) followed by 5-acetyl-1,3-dibenzyluracil (2a) (669 mg, 2 mmol) in THF (8 ml). The resulting mixture was stirred at room temperature for 4 h and then was acidified to pH=2. THF was evaporated. The residue in CH2Cl2 (100 ml) was washed with brine (20 ml) and purified by column chromatography (hexane:ethyl acetate, 2:1). The appropriate fraction was concentrated and crystallized from ethanol to give 254 mg of a yellow solid. Yield was 29.1%. Mp. 158-159° C. 1HNMR (CDCl3): 15.04 (s, br, 1H), 8.36 (s, 1H), 7.72 (s, 1H), 7.29-7.49 (m, 10H), 5.18 (s, 2H), 5.05 (s, 2H), 3.92 (s, 3H). 13CNMR (CDCl3): 185.7, 168.8, 162.4, 159.7, 150.5, 148.5, 136.0, 134.0, 129.4, 129.1, 129.0, 128.5, 128.3, 127.9, 109.0, 101.6, 53.7, 53.2, 45.0. FAB-HRMS: [M+H]+ calcd. for C23H21N2O6 421.1400, found 421.1418.

Workup

  1. customTHF was evaporated
  2. washThe residue in CH2Cl2 (100 ml) was washed with brine (20 ml)
  3. custompurified by column chromatography (hexane:ethyl acetate, 2:1)
  4. concentrationThe appropriate fraction was concentrated
  5. customcrystallized from ethanol

Sources & evidence

ORD record
ord-b9f603949eea432ba93a50b258ca3e8d
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Reaction notes

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