Trifluoroacetic acid → HCID 11660865, compound

HRID 1452640Notes

Reaction equation

HRID 1452640 reaction equation
C(OC([N:8]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH3:42])=[CH:36][CH:35]=1)[C:9]1[N:20]2[C:16](=[CH:17][CH:18]=[N:19]2)[N:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][N:13]2[C@H:21]1[CH2:26][CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:41]([O:40][C:37]1[CH:36]=[CH:35][C:34]([NH:8][C:9]2[N:20]3[C:16](=[CH:17][CH:18]=[N:19]3)[N:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][N:13]3[C@H:21]2[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]2)=[CH:39][CH:38]=1)[CH3:42]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57526792HCID 57526792, compound

Product 1

HCID 11660865HCID 11660865, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (4 mL) solution containing tert-butyl (S)-3-{8-[tert-butoxycarbonyl-(4-ethoxyphenyl)amino]-6,7-dihydro-1,4,5,8a-tetraaza-s-indacen-5-yl}piperidine-1-carboxylate (0.693 mmol), trifluoroacetic acid (2 mL) was added with ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 16 hr. After the reaction, the reaction solution was poured into aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off and the residue was purified with PTLC {10% (2 mol/L ammonia/methanol)-methylene chloride} to obtain the title compound (97.0 mg).

Workup

  1. additionwas added with ice-
  2. temperaturecooling
  3. customAfter the reaction
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. distillationthe solvent was distilled off
  9. customthe residue was purified with PTLC {10% (2 mol/L ammonia/methanol)-methylene chloride

Sources & evidence

ORD record
ord-184e6ac7935c464687d455e6aa12de77
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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