Trifluoroacetic acid → HCID 67435330, compound

HRID 1663590Notes

Reaction equation

HRID 1663590 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)[CH2:11]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=[O:37].ClC1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([S:2]([CH3:1])=[O:37])=[CH:8][CH:7]=2)[N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)[CH2:11]2)=[CH:31][CH:30]=1)#[N:33]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 11612166HCID 11612166, compound

Product 1

HCID 67435330HCID 67435330, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R)-1-[(4-methylthiophenyl)(4-cyanophenyl)methyl]-3-[(4-cyanobenzoyl)amino]pyrrolidine (45.3 mg) in methylene chloride (2 mL) was added trifluoroacetic acid (31 μL) under ice-cooling and the mixture was stirred at room temperature or 30 minutes. Thereto was added m-chloroperbenzoic acid (23 mg) under ice-cooling and the mixture was stirred at the same temperature for 1 hour and then stirred at room temperature for 4 hours. To the reaction mixture was added an aqueous saturated sodium hydrogen carbonate solution and the organic layer was extracted by a diatomaceous earth column (Chem Elut; VARIAN Inc.). The extract was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=98:2→90:10). The resultant product was dissolved in t-buthanol and lyophilized to give (3R)-1-[(4-cyanophenyl)-(4-methylsulfinylphenyl)methyl]-3-[(4-cyanobenzoyl)amino]pyrrolidine (42.5 mg, yield: 91%) as a powder. MS(APCI) m/z: 469 [M+H]+

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 1 hour
  4. stirringstirred at room temperature for 4 hours
  5. extractionthe organic layer was extracted by a diatomaceous earth column (Chem Elut; VARIAN Inc.)
  6. concentrationThe extract was concentrated in vacuo
  7. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; chloroform/methanol=98:2→90:10)
  8. dissolutionThe resultant product was dissolved in t-buthanol

Sources & evidence

ORD record
ord-d5c99e04943349eba0fe102809d7b780
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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