Trifluoroacetic acid → HCID 89726033、化合物

To a solution of 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate 29 (1.0 g, 2.9 mmol) in DCM (20 mL) was added TFA (2.31 g, 20.3 mmol) at 0° C. The reaction mixture was stirred at RT for 4 h. TLC analysis indicated complete conversion of SM. Reaction was concentrated to remove excess of TFA and sticky solid so obtained was taken in DCM (20 mL). To this suspension, HATU (1.65 g, 4.34 mmol), NMM (293 mg, 2.9 mmol), 3-formylbenzoic acid (435 mg, 2.9 mmol), and DMAP (10 mg) were added. Reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. The reaction mixture was diluted with DCM and washed with water; organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The sticky solid so obtained was added to a solution of NaOH (65 mg, 1.6 mmol) in MeOH (5 mL). Reaction mixture was stirred at rt for 7 h. The reaction was monitored by TLC. When SM was completely consumed, reaction mixture was concentrated under vacuum. The solid was suspended in water and acidified to pH 6 using 1 N HCl. The suspension was filtered and the precipitate was triturated with ethanol to give 766 mg (20%) of 4-(3-formylbenzoyl)piperazine-2-carboxylic acid 32 as sticky solid.

1. customReaction
2. concentrationwas concentrated
3. customto remove excess of TFA and sticky solid
4. customso obtained
5. customReaction mixture
6. stirringwas stirred at RT for 16 h
7. washwashed with water
8. customorganic layer was separated
9. dry with materialdried over Na2SO4
10. concentrationconcentrated under reduced pressure
11. customThe sticky solid so obtained
12. customReaction mixture
13. stirringwas stirred at rt for 7 h
14. customWhen SM was completely consumed
15. customreaction mixture
16. concentrationwas concentrated under vacuum
17. filtrationThe suspension was filtered
18. customthe precipitate was triturated with ethanol

ORDレコード

ord-e35ea073a762484baee916053c96c33f

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09238656B2