Trifluoroacetic acid → HCID 86585769, compound

HRID 393986Notes

Reaction equation

HRID 393986 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([NH:20][C:21]([C@@H:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:25][N:24]2C(OC(C)(C)C)=O)=[O:22])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([NH:20][C:21]([C@@H:23]2[CH:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:25][NH:24]2)=[O:22])[CH2:16][CH2:15]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 131724628HCID 131724628, compound

Product 1

HCID 86585769HCID 86585769, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-3-phenyl-[(2S)-2-pyrrolidinecarboxylic acid] (4-benzhydrylpiperazine-1-yl) amide (15) (2.70 g; 5.14 mmol) is dissolved in methylene chloride (30 mL) at ambient temperature. Trifluoroacetic acid (20 mL) is added in a slow stream, and the solution is stirred for 2 hours at ambient temperature. The reaction mixture is cooled in an ice-bath and the pH adjusted to 9 with saturated potassium carbonate solution. The mixture is poured onto water (30 mL) and extracted with methylene chloride (1×60 mL, 2×20 mL). The combined organic extracts are washed with water, dried over MgSO4, filtered, and concentrated in vacuo affording the desired product. CIMS: MH+ 426

Workup

  1. temperatureThe reaction mixture is cooled in an ice-bath
  2. additionThe mixture is poured onto water (30 mL)
  3. extractionextracted with methylene chloride (1×60 mL, 2×20 mL)
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a74f54691a84eb3b540e2a2327681a1
Source dataset
uspto-grants-2004_10
Patent number
US06809093B2

Reaction notes

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