Trifluoroacetic acid → HCID 66621762, compound

HRID 416016Notes

Reaction equation

HRID 416016 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[C:27]([Cl:29])[C:26]([CH2:30][CH:31]3[CH2:35][CH2:34][N:33]([CH:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)[C:32]3=[O:42])=[C:25]([Cl:43])[CH:24]=2)=[CH:19][CH:18]=1)=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:36]1([N:33]2[CH2:34][CH2:35][CH:31]([CH2:30][C:26]3[C:27]([Cl:29])=[CH:28][C:23]([C:20]4[CH:21]=[CH:22][C:17]([C:15]([N:11]5[CH2:10][CH:9]6[CH2:14][CH:12]5[CH2:13][NH:8]6)=[O:16])=[CH:18][CH:19]=4)=[CH:24][C:25]=3[Cl:43])[C:32]2=[O:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66621867HCID 66621867, compound

Product 1

HCID 66621762HCID 66621762, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve chiral 5-[3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-carbonyl]-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.119 g, 0.19 mmol) in dichloromethane (3 mL), treat with trifluoroacetic acid (1 mL) and stir for 1 hour at room temperature. Remove the solvent under vacuum, dissolve the residue in ethyl acetate and wash with saturated aqueous sodium bicarbonate then water. Dry the organic layer with sodium sulfate, concentrate under vacuum and purify the crude product by silica gel chromatography using a gradient of 0 to 10% methanol in dichloromethane to afford 100 mg (100%) of the title compound: MS (m/z): 526 (M+).

Workup

  1. customRemove the solvent under vacuum
  2. dissolutiondissolve the residue in ethyl acetate
  3. washwash with saturated aqueous sodium bicarbonate
  4. dry with materialDry the organic layer with sodium sulfate
  5. concentrationconcentrate under vacuum
  6. custompurify the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-25752b16a60840ddbe676aa525190a42
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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