Trifluoroacetic acid → N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]-glycinamide trifluoroacetate

HRID 58331Notes

Reaction equation

HRID 58331 reaction equation
C(O[C:6]([N:8](C)[CH2:9][C:10]([N:12]([CH3:35])[CH2:13][CH2:14][CH2:15][P+:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])=O)(C)(C)C.[Br-].[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>>[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[CH3:35][N:12]([CH2:13][CH2:14][CH2:15][P+:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:10](=[O:11])[CH2:9][NH:8][CH3:6]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131736995N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide

Product 1

HCID 131736997N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]-glycinamide trifluoroacetate

Procedure

N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide (280 mg, 0.48 mmol) was dissolved in trifluoroacetic acid (1.9 mL, 25 mol) at room temperature. After 30 minutes, the volatiles were removed under high vacuum and the crude product taken up in methylene chloride and washed with aqueous NaHCO3. The organic layer was then washed with water and concentrated to give the title compound in quantitative yield.

Workup

  1. customthe volatiles were removed under high vacuum
  2. washwashed with aqueous NaHCO3
  3. washThe organic layer was then washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2552db1de1a3438f89394ff526568560
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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