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Citric Acid → HCID 69079708, compound

HRID 1926936
Notes
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Reaction equation

HRID 1926936 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH:20]([OH:22])[CH3:21])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:5][CH:4]=1.C([O:33][C:34](=[O:37])[CH:35]=[CH2:36])(C)(C)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.FC(F)(F)C(O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][CH2:19][CH:20]([CH3:21])[O:22][CH2:36][CH2:35][C:34]([OH:37])=[O:33])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 311Citric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 15458tert-Butyl acrylateHCID 69076856HCID 69076856, compound

Product 1

HCID 69079708HCID 69079708, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Put 100 mg (0.27 mmol) (+)-1-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}-propan-2-ol with 170 mg (1.33 mmol) acrylic acid tert.-butyl ester and 18.1 mg (0.053 mmol) tetra-n-butylammonium hydrogensulphate in 2 ml dichloromethane and cool to 0° C. Then add 250 μl 50% sodium hydroxide solution and stir the mixture vigorously at 0° C. for 1 h. Leave to return to RT and continue stirring overnight at RT. Then dilute with dichloromethane and water. Acidify with 10% citric acid solution and separate the phases. Re-extract the aqueous phase once with dichloromethane. Combine the organic phases, wash once with satd. sodium chloride solution, dry over magnesium sulphate and concentrate by evaporation. Dissolve the residue thus obtained in 2.5 ml dichloromethane, add 600 μl trifluoroacetic acid and stir for a further 2 h at RT. Then concentrate by evaporation and purify the residue by chromatographing twice on a silica-gel thick-layer plate (solvent: dichloromethane/methanol 9:1). Extract the product zone with dichloromethane/methanol 9:1. After concentrating by evaporation and drying, 38 mg (42.8% of theor.) of the target compound is obtained.

Workup

  1. customLeave
  2. customto return to RT
  3. stirringcontinue stirring overnight at RT
  4. customseparate the phases
  5. washwash once with satd
  6. dry with materialsodium chloride solution, dry over magnesium sulphate
  7. concentrationconcentrate by evaporation
  8. dissolutionDissolve the residue
  9. customthus obtained in 2.5 ml dichloromethane
  10. stirringstir for a further 2 h at RT
  11. concentrationThen concentrate by evaporation
  12. custompurify the residue by chromatographing twice on a silica-gel thick-layer plate (solvent: dichloromethane/methanol 9:1)
  13. extractionExtract the product zone with dichloromethane/methanol 9:1
  14. concentrationAfter concentrating by evaporation
  15. customdrying
  16. custom38 mg (42.8% of theor.) of the target compound is obtained

Sources & evidence

ORD record
ord-60d4083bbe86484690f237801d1b18b0
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183246B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes