Triethylamine → 4-Fluoro-L-proline

13.0 mL of acetonitrile, 3.50 g (34.59 mmol, 3.46 eq) of triethylamine, and 1.60 g (9.92 mmol, 0.99 eq) of triethylamine tris(hydrogen fluoride) complex, followed by lowering the inside temperature to −40° C. and then bubbling 2.00 g (19.60 mmol, 1.96 eq) of sulfuryl fluoride from a cylinder. The inside temperature was returned to room temperature, and stirring was conducted for 20 hours. Conversion of the reaction was found by gas chromatography measurement to be 100%. The reaction-terminated liquid was poured into a potassium carbonate aqueous solution [prepared from 6.30 g (45.58 mmol, 4.56 eq) of potassium carbonate and 100.0 mL of water], followed by extraction two times with 100.0 mL of ethyl acetate. The recovered organic layer was concentrated under reduced pressure, followed by vacuum drying, thereby obtaining a crude product of 4-fluoroproline derivative represented by the following formula,

1. customto −40° C.
2. customwas returned to room temperature
3. extractionfollowed by extraction two times with 100.0 mL of ethyl acetate
4. concentrationThe recovered organic layer was concentrated under reduced pressure
5. customdrying

ORDレコード

ord-d46b9794969840b49f0e30f2ffe12651

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08058412B2