Trifluoroacetic acid → HCID 12069573, compound

HRID 2117367Notes

Reaction equation

HRID 2117367 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:33]=[CH:34][C:35]=1[N+:36]([O-:38])=[O:37])[C:13]([C:15]1[N:23]2[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]2)=[C:17]([NH:24]C(=O)OC(C)(C)C)[C:16]=1[CH3:32])=[O:14].C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OC(C)C)(C)C>[NH2:24][C:17]1[C:16]([CH3:32])=[C:15]([C:13]([C:12]2[CH:33]=[CH:34][C:35]([N+:36]([O-:38])=[O:37])=[C:10]([O:9][CH3:8])[CH:11]=2)=[O:14])[N:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[CH:22]2

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12069571HCID 12069571, compound

Product 1

HCID 12069573HCID 12069573, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2.32 ml of trifluoroacetic acid are added dropwise to a solution of 643 mg (1.51 mmol) of tert-butyl 3-(3-methoxy-4-nitrobenzoyl)-2-methylindolizin-1-ylcarbamate in 20 ml of dichloromethane, cooled to 0° C. Once the introduction is complete, the medium is allowed to return to room temperature and it is stirred for 4 hours. The reaction medium is poured over a saturated aqueous potassium carbonate solution and extracted with ethyl acetate. The organic phase is separated after settling out, washed with a saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The crystals obtained are taken up in isopropyl ether, filtered off, washed with isopropyl ether and then dried. 425 mg of a brown solid are obtained.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crystals obtained
  8. filtrationfiltered off
  9. washwashed with isopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-2700da04f660456cbc1545bb9fc4ee44
Source dataset
uspto-grants-2008_10
Patent number
US07442708B2

Reaction notes

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