Trifluoroacetic acid → HCID 67464210, compound

HRID 469739Notes

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([O:18]C(C)(C)C)[CH2:15][N:14]2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][C@@H:16]([OH:18])[CH2:15][N:14]2[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67953453HCID 67953453, compound

Product 1

HCID 67464210HCID 67464210, compound

Procedure

(2S,4R)-4-tert-Butoxy-1-(4-chloro-phenyl)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (45 mg, 0.107 mmol) is dissolved in trifluoroacetic acid (0.5 mL, 6.49 mmol) at room temperature and the reaction is stirred at room temperature for 1 hour. The reaction is concentrated under reduced pressure and purification by chromatography on silica eluting with ethyl acetate/hexanes provides the title compound. ESI m/z 364 [M+H+].

Workup

concentrationThe reaction is concentrated under reduced pressure and purification by chromatography on silica eluting with ethyl acetate/hexanes

Sources & evidence

ORD record: ord-8a1067d8a30b482ea4b78d24be534716
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629157B2

Reaction notes

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