Trifluoroacetic acid → HCID 10222221, compound

HRID 1883611Notes

Reaction equation

HRID 1883611 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([S:29][CH2:30][CH2:31][CH3:32])[C:12]2[O:21][CH:20]3[CH:15]([CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19]3)[C:13]=2[CH:14]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([S:29][CH2:30][CH2:31][CH3:32])[C:12]2[O:21][CH:20]3[CH:15]([CH2:16][NH:17][CH2:18][CH2:19]3)[C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23508126HCID 23508126, compound

Product 1

HCID 10222221HCID 10222221, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 8-(2,4-dichlorophenyl)-6-(propylthio)-3,4,4a,9b-tetrahydro[1]benzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.090 g, 0.182 mmol) was dissolved in CH2Cl2 (5 mL). Trifluoracetic acid (0.3 mL, 0.182 mmol) was added and the reaction mixture was stirred at rt under N2 for 2.5 h when all the starting material was consumed. The reaction mixture was cooled to 0° C. and 5M NaOH (10 mL) was added. The reaction mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2 (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography (first eluting with 3:1 Hexane:EtOAc, and then eluting with 2:6:92 conc. NH4OH:CH3OH:CH2Cl2 to elute the product). Example 252 (0.070 g) was obtained in 97% yield. HRMS (FAB) calcd for C20H21CL2NOS +H1 394.0799, found 394.0797.

Workup

  1. customwas consumed
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. addition5M NaOH (10 mL) was added
  4. customThe reaction mixture was partitioned between CH2Cl2 and water
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude was purified by chromatography (
  10. washfirst eluting with 3:1 Hexane
  11. washEtOAc, and then eluting with 2:6:92 conc. NH4OH
  12. washCH3OH:CH2Cl2 to elute the product)

Sources & evidence

ORD record
ord-6247f9eccc1e44db931c366540f923c7
Source dataset
uspto-grants-2004_07
Patent number
US06762191B2

Reaction notes

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