Trifluoroacetic acid → HCID 69797549, compound

HRID 1072428Notes

Reaction equation

HRID 1072428 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C@H:10]([CH2:21][OH:22])[CH2:9]1)=O)(C)(C)C.[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26]>ClCCl>[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[CH2:14]([N:11]1[CH2:12][CH2:13][NH:8][CH2:9][C@H:10]1[CH2:21][OH:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 569778731,1-Dimethylethyl (3S)-4-heptyl-3-(hydroxymethyl)-1-piperazinecarboxylate

Product 1

HCID 69797549HCID 69797549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 1 (e) (0.53 g) in dichloromethane (20m1) and trifluoroacetic acid was stirred at 0° C. for 30 minutes and allowed to warm to room temperature over 2 hours. It was evaporated to dryness and azeotroped with toluene to afford [2S]-1-heptyl-2-hydroxymethylpiperazine trifluoroacetate salt as a foam. The salt was dissolved in acetonitrile (3 ml), and treated with diusopropylethylamine (0.544 g) until pH 6. Example 1(f) (0.509 g) and lithium perchlorate (0.179 g) were added and the mixture was stirred at room temperature for 48 hours. [method of J. E. Chateauneuf et al. J. Org. Chem. 56, 5939-5942]. The reaction rriixture was evaporated and basified with sodium carbonate solution and extracted (x3) with dichloromethane. The organic fraction was dried and chromatographed on silica gel eluting with 50-100% ethyl acetate-hexane to afford the title compound as an oil (0.248 g).

Workup

  1. customIt was evaporated to dryness
  2. customazeotroped with toluene

Sources & evidence

ORD record
ord-95b58695cbfc44868aa19a3e630f2369
Source dataset
uspto-grants-2005_06
Patent number
US06911442B1

Reaction notes

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