Trifluoroacetic acid → (R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-(2-methoxy-ethyl)-amino]-propionyl]-pyrrolidine-2-carboxylic acid trifluoroacetate

HRID 1636152Notes

Reaction equation

HRID 1636152 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:37])[CH2:14][CH2:15][N:16]([CH2:21][CH2:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@@H:26]1[C:30]([O:32]C(C)(C)C)=[O:31])=[O:24])[CH2:17][CH2:18][O:19][CH3:20])=[O:7])(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>ClCCl.O>[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41].[C:30]([C@H:26]1[CH2:27][CH2:28][CH2:29][N:25]1[C:23](=[O:24])[CH2:22][CH2:21][N:16]([CH2:17][CH2:18][O:19][CH3:20])[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:37])([OH:32])=[O:31]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54193295(R)-1-[3-[[3-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-(2-methoxy-ethyl)-amino]-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 69895993(R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-(2-methoxy-ethyl)-amino]-propionyl]-pyrrolidine-2-carboxylic acid trifluoroacetateYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 150 mg (0.29 mmol) (R)-1-[3-[[3-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-(2-methoxy-ethyl)-amino]-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 lyophilisation, 100 mg (67%) of the title compound as a yellow oil. MS m/e (%): 436 (M+Na+, 35), 414 (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-6970bf4df23d4e1f82c3919c788b7ca6
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

Loading…