Trifluoroacetic acid → 4,4-difluoro-N,N-dimethyl-L-prolinamide trifluoroacetate

HRID 490128Notes

Reaction equation

HRID 490128 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][N:9]([CH3:26])[C:10]([C@@H:12]1[CH2:16][C:15]([F:18])([F:17])[CH2:14][N:13]1C(OC(C)(C)C)=O)=[O:11]>C(Cl)(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:18][C:15]1([F:17])[CH2:14][NH:13][C@H:12]([C:10]([N:9]([CH3:8])[CH3:26])=[O:11])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25178383BOC-4,4-difluoroproline-N,N-dimethylamide

Product 1

HCID 674283014,4-difluoro-N,N-dimethyl-L-prolinamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

11 mL of trifluoroacetic acid was added under ice cooling to a 40 mL chloroform solution of 3.85 g of the compound obtained in step 3-4, and the reaction mixture was stirred for 2 hours at room temperature. The solvent was then distilled off under reduced pressure to obtain 8.02 g of residue (pale yellow oily substance). This compound was used in the following reaction without being purified.

Workup

  1. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-e507d1faf8cf47ee96c626590ec66f0d
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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