Trifluoroacetic acid → HCID 69894157, compound

HRID 1636156Notes

Reaction equation

HRID 1636156 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:33])[CH2:14][CH2:15][NH:16][CH2:17][CH2:18][C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@@H:22]1[C:26]([O:28]C(C)(C)C)=[O:27])=[O:20])=[O:7])(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>ClCCl.O>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[C:26]([C@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:19](=[O:20])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([OH:7])=[O:5])=[O:33])([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53743320HCID 53743320, compound

Product 1

HCID 69894157HCID 69894157, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 33 mg (0.07 mmol) (R)-1-[3-[3-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-3-oxo-propylamino]-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester in 5 ml dichloromethane at 0° C. was added dropwise 1.0 ml 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, after resuspension in water and subsequent lyophilization, 19 mg (76%) of the title compound as a yellow glassy solid. MS m/e (%): 354 ([M−H]−, 100).

Workup

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

Sources & evidence

ORD record
ord-0ef88aef277e43d9a36778b8d3f84368
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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