Trifluoroacetic acid → HCID 57892091, compound

HRID 1820873Notes

Reaction equation

HRID 1820873 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:40])[CH2:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:30][CH:29]=3)=[O:27])=[CH:19][C:18]=2[Cl:41])[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:40])[CH2:25][C:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:32][CH:33]=3)=[O:27])=[CH:19][C:18]=2[Cl:41])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86601366HCID 86601366, compound2×

Product 1

HCID 57892091HCID 57892091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.19 g (0.33 mmol) of N-{4-[2-(4-tert-butoxycarbonylaminopiperidin-1-yl)ethyl]-3-chlorophenyl}-3-biphenyl-4-yl-3-oxopropionamide (compound 1.41) is dissolved in 7 mL of methylene chloride, 500 mL of trifluoroacetic acid is added, and the mixture is stirred for 12 hours at ambient temperature. After this time, saturated sodium hydrogen carbonate solution is added and the precipitate formed is suction filtered. The residue is dried in vacuo over sodium hydroxide. Yield: 160 mg (100% of theory); Rf value: 0.10 (silica gel, methylene chloride/methanol=9:1); m.p. above 144° C. (decomposition); C28H30ClN3O2; EII mass spectrum: m/z=476/478 [M+H]+.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. dry with materialThe residue is dried in vacuo over sodium hydroxide

Sources & evidence

ORD record
ord-00494137e41c49e99ac3b43f3d7b1415
Source dataset
uspto-grants-2009_10
Patent number
US07605176B2

Reaction notes

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