Dichloromethane → Trifluoroacetic acid

HRID 1920567Notes

Reaction equation

HRID 1920567 reaction equation
F[P-](F)(F)(F)(F)F.C(OC([N:15]1[CH2:18][CH:17]([C:19]([NH:21][CH2:22][CH2:23][N+:24]23[CH2:31][CH2:30][CH:27]([CH2:28][CH2:29]2)[C@@H:26]([O:32][C:33](=[O:48])[C:34]([OH:47])([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:25]3)=[O:20])[CH2:16]1)=O)(C)(C)C.[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50].C(Cl)Cl>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:52][C:51]([F:54])([F:53])[C:49]([OH:55])=[O:50].[F:52][C:51]([F:54])([F:53])[C:49]([O-:55])=[O:50].[NH:15]1[CH2:18][CH:17]([C:19]([NH:21][CH2:22][CH2:23][N+:24]23[CH2:31][CH2:30][CH:27]([CH2:28][CH2:29]2)[C@@H:26]([O:32][C:33](=[O:48])[C:34]([OH:47])([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:25]3)=[O:20])[CH2:16]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86639173HCID 86639173, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67495520HCID 67495520, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

(R)-1-(2-[(1-tert-butoxycarbonyl-azetidine-3-carbonyl)-amino]ethyl]-3-(2-hydroxy-2,2-diphenyl-acetoxy)1-azonia-bicyclo[2.2.2]octane hexafluorophosphate is dissolved in TFA:DCM (1:1) (2 ml) and stirred at room temperature for 1 hour. TFA:DCM (2 ml) is added to the reaction mixture to complete the reaction. The solvent is removed in vacuo and purification of the crude residue by mass directed preparative HPLC eluting with water:acetonitrile:trifluoroacetic acid yields the titled compound.

Workup

  1. customthe reaction
  2. customThe solvent is removed in vacuo and purification of the crude residue by mass
  3. washeluting with water

Sources & evidence

ORD record
ord-fa1bc6ae09124f3780cfef0c34443ee0
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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