Trifluoroacetic acid → Trifluoroacetic acid

HRID 1889144Notes

Reaction equation

HRID 1889144 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.[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[CH2:30]([NH:37][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:16])=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7504BenzylamineHCID 86666090HCID 86666090, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67775295HCID 67775295, 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 benzylamine (47.7 μL, 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 (7.3 mg). MS m/z: [M+H]+ calcd for C20H23F3N2O3S, 429.14. found 429.0.

Workup

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

Sources & evidence

ORD record
ord-d36ccc819c8c4cb785f37ca049b529f2
Source dataset
uspto-grants-2013_08
Patent number
US08501964B2

Reaction notes

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