Trifluoroacetic acid methylene chloride → 2-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)

HRID 251723Notes

Reaction equation

HRID 251723 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:17]1[NH:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][N:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15])(C)(C)C.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30].C(Cl)Cl>>[F:32][C:31]([F:34])([F:33])[C:29]([O-:35])=[O:30].[F:32][C:31]([F:34])([F:33])[C:29]([O-:35])=[O:30].[NH3+:7][C@H:8]([C:17]1[NH2+:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][N:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 91226371tert-Butyl[(1S)-7-oxo-1-(5-phenyl-1H-imidazol-2-yl)octyl]carbamate

Product 1

HCID 866279482-[(1S)-1-Ammonio-7-oxooctyl]-5-phenyl-1H-imidazol-1-ium bis(trifluoroacetate)

Procedure

A2 (1 eq.) was dissolved in TFA/DCM (1:1) at 0° C. The cooling bath was removed and the mixture was stirred for 60 min at RT. The solvents were removed under reduced pressure and the residue was left under high vacuum for a further 3 h. The crude amine salt A3 was used without further purification. MS (ES) C17H23N3O requires: 285, found: 286 (M+H)+.

Workup

  1. customThe cooling bath was removed
  2. customThe solvents were removed under reduced pressure
  3. waitthe residue was left under high vacuum for a further 3 h
  4. customThe crude amine salt A3 was used without further purification

Sources & evidence

ORD record
ord-efdaf96dfecd46cb85600f4193814f42
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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