Trifluoroacetic acid → HCID 68451633, compound

HRID 902891Notes

Reaction equation

HRID 902891 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[NH:27][C:28]([C:30]1[N:31]=[CH:32][C:33]3[CH2:38][N:37]([C:39](OC(C)(C)C)=O)[CH2:36][C:34]=3[N:35]=1)=[O:29])=[O:19])=[CH:12]2>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]1[NH:27][C:28]([C:30]1[N:31]=[CH:32][C:33]3[CH2:38][N:37]([CH3:39])[CH2:36][C:34]=3[N:35]=1)=[O:29])=[O:19])=[CH:12]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58822249HCID 58822249, compound

Product 1

HCID 68451633HCID 68451633, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of the compound (34.0 mg) obtained in Example 32 dissolved in methylene chloride (1 ml) at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride (1 ml), to which triethylamine (17.6 μl), acetic acid (7.21 μl), 35% formalin (8.13 μl) and sodium triacetoxyborohydride (20.1 mg) were added at room temperature. The resultant mixture was stirred for 1 hour. Methylene chloride (10 ml) and saturated aqueous solution (10 ml) of sodium hydrogencarbonate were added to the reaction mixture to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:methylene chloride=7:93). A 1N ethanol solution of hydrochloric acid and ethyl acetate were added to the product thus obtained to solidify it, and the resultant solids were collected by filtration to obtain the title compound (8.0 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (1 ml), to which triethylamine (17.6 μl), acetic acid (7.21 μl), 35% formalin (8.13 μl) and sodium triacetoxyborohydride (20.1 mg)
  3. additionwere added at room temperature
  4. stirringThe resultant mixture was stirred for 1 hour
  5. additionMethylene chloride (10 ml) and saturated aqueous solution (10 ml) of sodium hydrogencarbonate were added to the reaction mixture
  6. customto separate an organic layer
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (methanol:methylene chloride=7:93)
  10. additionA 1N ethanol solution of hydrochloric acid and ethyl acetate were added to the product
  11. customthus obtained
  12. filtrationthe resultant solids were collected by filtration

Sources & evidence

ORD record
ord-d275035c2fdb49b09fcee3bafe17f846
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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