Sodium Bicarbonate → Trifluoroacetic acid

(S)-3-[(S)-2-Amino-1-(4-trifluoromethylphenoxy)ethyl]pyrrolidine-1-carboxylic acid t-butyl ester (35.0 mg, 0.093.5 mol, 1.0 eq.) was dissolved in DCM (1.2 mL) and triethylamine (39.1 μL). A solution of 4-(1,3-oxazol-5-yl)benzenesulfonyl chloride (56.9 mg, 234 μmol, 2.5 eq.) in DCM (0.4 mL,) was then added. The resulting mixture was stirred for 1 hour at room temperature. Saturated sodium bicarbonate was then added (1 mL) and the mixture was diluted with DCM (2 mL). The organic layer was collected and concentrated under reduced pressure. The crude material was redissolved in 1.2 M of HCl in EtOH (1.9 mL) and stirred at room temperature overnight. The mixture was then concentrated under reduced pressure then redissolved in 1:1 AcOH/H2O (1.5 mL) and purified by preparative HPLC to yield the title compound as a TFA salt (20.1 mg). MS m/z: [M+H]+ calcd for C22H22F3N3O4S, 482.13. found 482.4.

1. customThe organic layer was collected
2. concentrationconcentrated under reduced pressure
3. dissolutionThe crude material was redissolved in 1.2 M of HCl in EtOH (1.9 mL)
4. stirringstirred at room temperature overnight
5. concentrationThe mixture was then concentrated under reduced pressure
6. dissolutionthen redissolved in 1:1 AcOH/H2O (1.5 mL)
7. custompurified by preparative HPLC

ORDレコード

ord-644aed644df345d58fcac156f420d607

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08637568B2