Trifluoroacetic acid → HCID 22717150, compound

HRID 1636161Notes

Reaction equation

HRID 1636161 reaction equation
C([O:5][C:6]([C:8]1[N:9]([C:13](=[O:32])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([N:20]2[CH:24]=[CH:23][CH:22]=[C:21]2[C:25]([O:27]C(C)(C)C)=[O:26])=[O:19])[CH:10]=[CH:11][CH:12]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:25]([C:21]1[N:20]([C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][C:13]([N:9]2[CH:10]=[CH:11][CH:12]=[C:8]2[C:6]([OH:7])=[O:5])=[O:32])[CH:24]=[CH:23][CH:22]=1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54431429HCID 54431429, compound

Product 1

HCID 22717150HCID 22717150, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 55 mg (0.12 mmol) 1-[6-(2-tert-butoxycarbonyl-pyrrol-1-yl)-6-oxo-hexanoyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester in 8 ml dichloromethane at 0° C. was added dropwise 0.15 ml (1.97 mmol) trifluoroacetic acid and stirring continued for 16 h at room temperature. Concentration in vacuo and azeotroping three times with chloroform on a rotary evaporator afforded 39 mg (95%) of the title compound as an off-white crystalline solid. MS m/e (%): 350 (M+NH4+, 100).

Workup

  1. concentrationConcentration in vacuo
  2. customazeotroping three times with chloroform
  3. customon a rotary evaporator

Sources & evidence

ORD record
ord-4e63962142cf47e98e058f81dcd75a03
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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