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Potassium Carbonate → HCID 178491256, compound

HRID 1727323
Notes
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Reaction equation

HRID 1727323 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 6228DimethylformamideSolvent
HCID 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-0b244cd8d37a4dac976760796697d087
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495006B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes