Trifluoroacetic acid → HCID 58493941, compound

HRID 2360485Notes

Reaction equation

HRID 2360485 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[C:8]([O:45][CH3:46])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:44])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([C@H:32]3[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[C:8]([O:45][CH3:46])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:44])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([C@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58493955HCID 58493955, compound

Product 1

HCID 58493941HCID 58493941, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

220 mg tert-butyl (S)-3-{4-[2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-ylmethyl]-piperazine-1-carbonyl}-pyrrolidine-1-carboxylate are dissolved in 5 ml dichloromethane, combined with 231 μl trifluoroacetic acid and stirred for 12 hours at ambient temperature. Then the solvents are eliminated in vacuo, divided between saturated aqueous sodium hydrogen carbonate solution and dichloromethane and stirred vigorously for 30 minutes. The phases are separated, the aqueous phase is extracted twice with dichloromethane and the combined organic phases are dried on magnesium sulphate. Then the solvents are eliminated in vacuo and the crude product is chromatographed on silica gel (dichloromethane/(methanol-conc. ammonia 9:1) 90:10 to 80:20).

Workup

  1. stirringstirred vigorously for 30 minutes
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with dichloromethane
  4. customthe combined organic phases are dried on magnesium sulphate
  5. customthe crude product is chromatographed on silica gel (dichloromethane/(methanol-conc. ammonia 9:1) 90:10 to 80:20)

Sources & evidence

ORD record
ord-0402ef4a768f4a16ac753f84fa6c7877
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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