Potassium Carbonate → HCID 178491256, compound

HRID 1641510Notes

Reaction equation

HRID 1641510 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:14][C@H:13](CS([O-])(=O)=O)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]([CH2:23][C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1)=[N+:21]=[N-:22].[F:32][C:33]1[C:34](=[O:40])[NH:35][C:36](=[O:39])[NH:37][CH:38]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>O.CCOC(C)=O.CN(C=O)C>[N:20]([CH2:23][C:24]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[CH:26][CH:25]=1)=[N+:21]=[N-:22].[F:32][C:33]1[C:34](=[O:40])[NH:35][C:36](=[O:39])[N:37]([C@H:13]2[CH2:12][C@@H:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14]2)[CH:38]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 131727295HCID 131727295, compoundHCID 178527650HCID 178527650, compound

Product 1

HCID 178491256HCID 178491256, compoundYield 50.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

In a 50 mL three-neck flask with trans-3-(benzyloxyethyl)cyclobutyl-mesylate (0.34 g, 1.2 mmol), N3-PMB-5-fluoro-uracil (0.36 g, 1.44 mmol), K2CO3 (0.2 g, 1.44 mmol) and 18-crown-6 (0.38 g, 1.44 mmol) inside, dry DMF 10 mL was added under argon to give a light yellow solution with some white solids at the bottom of the flask. After 5 min, start to heat to 120° C. After 24 hr, add 30 mL EtOAc and 20 mL H2O. The organic phase was separated and washed with brine once. The organic phase was dried over MgSO4 and the solvents were evaporated to give the crude product, which was purified by silica gel flash chromatography (Hexane: EtOAc=3:1) to give an off-white solid (0.27 g, 50.9%) combined with some three-membered ring by-products. 1H NMR (CDCl3, 300 MHz): δ 1.72-1.79 (m, 4H), 2.16-2.24 (m, 1H), 2.51-2.60 (m, 2H), 3.43-3.48 (m, 2H), 3.77 (s, 3H), 4.48 (s, 2H), 4.64-4.75 (m, 1H), 5.05 (s, 2H), 6.81-6.84 (d, J=9.0, 2H), 7.29-7.36 (m, 6H), 7.44-7.47 (d, J=9.0, 2H). MS (FAB): expected for C25H27FN2O4 (M+H)+ 439.49. Found 439.20320. IR (neat) νmax 2926, 2854, 1712, 1458, 1377, 1265, 895, 740, 705.

Workup

  1. customto give a light yellow solution with some white solids at the bottom of the flask
  2. waitAfter 24 hr
  3. customThe organic phase was separated
  4. washwashed with brine once
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvents were evaporated
  7. customto give the crude product, which
  8. customwas purified by silica gel flash chromatography (Hexane: EtOAc=3:1)

Sources & evidence

ORD record
ord-ba12f2a35f69443d8129ea296e696ece
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

Loading…