Trifluoroacetic acid → HCID 22139406, compound

HRID 1825794Notes

Reaction equation

HRID 1825794 reaction equation
C(OC(=O)[NH:7][C:8]1[C:21]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([C:22]2[O:23][C:24]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][C:26](=[O:28])[CH:27]=2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][C:8]1[C:21]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([C:22]2[O:23][C:24]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:25][C:26](=[O:28])[CH:27]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590615HCID 86590615, compound

Product 1

HCID 22139406HCID 22139406, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-1-yl]-carbamic acid tert-butyl ester (3.25 g) in CH2Cl2 (25 ml) was added trifluoroacetic acid (5 ml). The mixture was stirred at room temperature for 18 hrs whereupon it was cooled (0° C.) and quenched by dropwise addition of saturated NaHCO3 until the pH 9 was attained. The mixture was then extracted using CH2Cl2 (3×20 mL), the combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give a semi-crystalline solid that was applied onto a thin silica pad and eluted with EtOAc (100%) going to EtOAc:MeOH (9:1). The eluent was concentrated in vacuo to give the title compound as a mild amber oil (1.46 g, 56.4% over three steps) m/z (LC-MS, ESP): 393 [M+H]+, R/T=3.79 mins

Workup

  1. temperaturewas cooled (0° C.)
  2. customquenched by dropwise addition of saturated NaHCO3 until the pH 9
  3. extractionThe mixture was then extracted
  4. dry with materialthe combined organic extracts were then dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a semi-crystalline solid
  8. washeluted with EtOAc (100%)
  9. concentrationThe eluent was concentrated in vacuo

Sources & evidence

ORD record
ord-53c4bdbb2a154bcc9341187e7e5e0184
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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