Ammonia → Trifluoroacetic acid

HRID 1889143Notes

Reaction equation

HRID 1889143 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.[NH3:30].O1CCOCC1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[NH: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]([NH2:30])(=[O:17])=[O:16])[CH2:9]1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 86666090HCID 86666090, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 67776143HCID 67776143, 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 0.5 M of ammonia in 1,4-dioxane (874 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 (16.3 mg). MS m/z: [M+H]+ calcd for C13H17F3N2O3S, 339.09. found 339.0.

Workup

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

Sources & evidence

ORD record
ord-1f084ca8cca54ce48b8ceff1b8517e46
Source dataset
uspto-grants-2013_08
Patent number
US08501964B2

Reaction notes

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