Triethylamine → HCID 58356111, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)[C@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P([N:37]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:37][C@H:10]1[C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=2)[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of the compound (2.29 g) obtained in step 8 in toluene (24.0 mL) were added DPPA (2.44 g) and triethylamine (1.23 mL), and the mixture was stirred at 65° C. for 1 hr. The mixture was cooled to −10° C., 8N aqueous sodium hydroxide solution (9.23 mL) was added dropwise, and the mixture was stirred at −10° C. to 0° C. for 1.5 hr. The mixture was diluted with toluene, and extracted with water and 1N aqueous sodium hydroxide solution. The combined aqueous layer was extracted with ethyl acetate (4 times), dried and concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (1.83 g, 88%) as a yellow oil.
Workup
- temperatureThe mixture was cooled to −10° C.
- stirringthe mixture was stirred at −10° C. to 0° C. for 1.5 hr
- extractionextracted with water and 1N aqueous sodium hydroxide solution
- extractionThe combined aqueous layer was extracted with ethyl acetate (4 times)
- customdried
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with ethyl acetate
- filtrationthe insoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-41ef678b48194542b09e21cadc40c315
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592454B2
Reaction notes
Loading…