Trifluoroacetic acid → HCID 68687668, compound

HRID 2245346Notes

Reaction equation

HRID 2245346 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[C@H:10]([C:25]([N:27]2[CH2:31][CH2:30][S:29][CH2:28]2)=[O:26])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:18]([O:17][C:15](=[O:16])[NH:14][C@H:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68688001HCID 68688001, compound

Product 1

HCID 68687668HCID 68687668, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R, 4S)-4-Benzyloxycarbonylamino-3-(thiazolidine-3-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester (325 mg) was dissolved in abs. DCM (12 ml) and TFA (0.44 ml) was added dropwise. The resulting mixture was then allowed to stir at RT over night and was then evaporated. The residue was transferred into ice/brine, basified to pH 10 with 2N NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated to give a residue that was purified by flash chromatography to give the desired product as a white foam (260 mg). MS (ESI): 350.1 MH+).

Workup

  1. customwas then evaporated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a residue that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-72419460dd1149d1843685cbbdd0f494
Source dataset
uspto-grants-2010_03
Patent number
US07683079B2

Reaction notes

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