Methylamine → Trifluoroacetic acid

HRID 1889145Notes

Reaction equation

HRID 1889145 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@H:13]([O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:14][S:15](Cl)(=[O:17])=[O:16])[CH2:9]1)=O)(C)(C)C.[CH3:30][NH2:31].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[CH3:30][NH:31][S:15]([CH2:14][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)(=[O:17])=[O:16].[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 6422Trifluoroacetic acidHCID 86666090HCID 86666090, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67776294HCID 67776294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-[(S)-2-Chlorosulfonyl-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester (50 mg, 109 μmol, 1.0 eq.) in DCM (1.0 mL) was combined with a solution of methylamine (2M in THF; 4.0 eq) and the resulting mixture was stirred at room temperature for 2 hours. TFA (1.0 mL) was added and stirred for 1 minute. The mixture was then concentrated and purified by preparative HPLC to yield the title compound as a TFA salt (8.7 mg). MS m/z: [M+H]+ calcd for C14H19F3N2O3S, 353.11. found 353.0.

Workup

  1. stirringstirred for 1 minute
  2. concentrationThe mixture was then concentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-a3f81368205a495d885efdb33b2de762
Source dataset
uspto-grants-2013_08
Patent number
US08501964B2

Reaction notes

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