Toluene → HCID 178470718, compound

HRID 2293625Notes

Reaction equation

HRID 2293625 reaction equation
C(OC([NH:8][C@H:9]([C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]1)=[O:21])[CH2:10][CH2:11][CH2:12][NH:13][C:14](=[NH:19])[NH:15][N+:16]([O-:18])=[O:17])=O)(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].C1(C)C=CC=CC=1>ClCCl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[N+:16]([NH:15][C:14](=[NH:19])[NH:13][CH2:12][CH2:11][CH2:10][C@@H:9]([C:20]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]1)=[O:21])[NH2:8])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 178470715HCID 178470715, compound

Product 1

HCID 178470718HCID 178470718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-((S)-Nα -t-butoxycarbonyl-Nω -nitroarginyl)-4-(ethoxycarbonylmethyl)piperidine (1.2 g) in dichloromethane (25 ml) cooled to 0° to 5° C. is slowly added trifluoroacetic acid (2.8 g) and the reaction mixture is allowed to warm to room temperature and is then stirred for 6 hours. Toluene (30 ml) is then added and the mixture is concentrated by evaporation and then co-evaporated with further toluene portions (2×30 ml) and the eventual residue is triturated with ether, collected by filtration, washed with ether and dried to constant weight in vacuo to give 1-((S)-Nω -nitroarginyl)-4-(ethoxycarbonylmethyl)-piperidine trifluoroacetate as a white solid, Rf (BuOH/CH3COOH/H2O 3:2:1)=0.50.

Workup

  1. concentrationthe mixture is concentrated by evaporation
  2. customthe eventual residue is triturated with ether
  3. filtrationcollected by filtration
  4. washwashed with ether
  5. customdried to constant weight in vacuo

Sources & evidence

ORD record
ord-927317931d6f48b39cf618f45ca8fa89
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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