Trifluoroacetic acid → HCID 178520673, compound

HRID 2289078Notes

Reaction equation

HRID 2289078 reaction equation
[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[O:35])[NH:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][C@H:21]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]2)=[O:19])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52]>ClCCl.ClCCCl>[F:49][C:50]([F:55])([F:54])[C:51]([OH:53])=[O:52].[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10]([N:12]=[C:13]([NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=2)=[O:35])[NH:14][CH2:15][CH2:16][CH2:17][C:18]([NH:20][C@H:21]2[CH2:25][CH2:24][NH:23][CH2:22]2)=[O:19])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452033HCID 178452033, compound

Product 1

HCID 178520673HCID 178520673, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound (2.50 g), which had been obtained in (1), in anhydrous dichloromethane (25 ml), trifluoroacetic acid (15 ml) was added dropwise under ice cooling, followed by stirring at the same temperature for 15 minutes and at room temperature for 15 minutes. The reaction mixture was diluted with 1,2-dichioroethane and concentrated by evaporation under reduced pressure. The residue was washed successively with hexane and diethyl ether by decantation and then the solvent was distilled off, whereby crude (3S)-3-[4-[2,3,-di(4-nitrobenzyloxycarbonyl)guanidino]butanoylamino]pyrrolidine trifluoroacetate (2.55 g) was obtained. The product was provided for use in the subsequent reaction without isolation.

Workup

  1. concentrationconcentrated by evaporation under reduced pressure
  2. washThe residue was washed successively with hexane and diethyl ether by decantation
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-13893cf886cd44e28fbf0e16b8bb6ec2
Source dataset
uspto-grants-2000_07
Patent number
US06090802

Reaction notes

Loading…