Hydrochloric Acid → HCID 11453384, compound

HRID 1790286Notes

Reaction equation

HRID 1790286 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10](=[O:38])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][C@@H:19]([C:22]([C:35](=[O:37])[NH2:36])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18]1)C)(C)(C)C.Cl.C(O)(C(F)(F)F)=O>C(Cl)Cl.O1CCOCC1>[CH3:6][NH:7][CH2:9][C:10]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][C@@H:19]([C:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:35]([NH2:36])=[O:37])[CH2:18]1)=[O:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69414505HCID 69414505, compound

Product 1

HCID 11453384HCID 11453384, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ({5-[(S)-3-(carbamoyldiphenylmethyl)pyrrolidin-1-yl]pentylcarbamoyl}methyl)methylcarbamic acid tert-butyl ester (23.47 g, 43.7 mmol) in DCM (60 mL) was added 4 N HCl in dioxane (100 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated to dryness. The residue was dissolved in water (100 mL) and this solution was washed with DCM (4×60 mL). The aqueous phase was then made basic with 20% aqueous potassium carbonate and extracted with DCM (4×60 mL). The combined organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was then dissolved in water (50 mL) containing TFA (2.5 eq) and purified by HPLC to obtain 17.5 g of the title compound as a bis(trifluoroacetate) salt. MS m/z [M+H+] calc'd for C26H36N4O2 437.3; found 437.5.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. washthis solution was washed with DCM (4×60 mL)
  4. extractionextracted with DCM (4×60 mL)
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe residue was then dissolved in water (50 mL)
  9. custompurified by HPLC

Sources & evidence

ORD record
ord-598b57d4432c433ab63bb311f3240ad0
Source dataset
uspto-grants-2006_07
Patent number
US07071224B2

Reaction notes

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