Tetrahydrofuran → HCID 178425720, Verbindung
Reaktionsgleichung
[NH2:1][C@@:2]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[CH:19][CH:18]=1)([C:13]([F:16])([F:15])[F:14])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].C1CCC(N=C=NC2CCCCC2)CC1.[N:46]1[N:47](CC(O)=O)[N:48]=[N:49][CH:50]=1.C1C[O:58][CH2:57][CH2:56]1>>[NH:46]1[C:50]([CH2:56][C:57]([NH:1][C:2]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][C:27]([F:28])([F:29])[F:30])=[CH:19][CH:18]=2)([CH2:3][C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)[C:13]([F:16])([F:15])[F:14])=[O:58])=[N:49][N:48]=[N:47]1Komponenten
5
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of Intermediate 2F (789 mg, 1.82 mmol) in anhydrous THF (9 ml) at 0° C. was added DCC (1.13 g, 5.46 mmol). 2-Tetrazole acetic acid (700 mg, 5.46 mmol) was added dropwise as a suspension in anhydrous THF (8 mL). The reaction was stirred at 0° C. for 1 h and then at rt overnight. The reaction was filtered and solids were rinsed with THF. The filtrate was diluted with EtOAc (40 mL), washed with sat'd Na2CO3 and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide Intermediate 2G (1.5 g, 152%) as a reddish brown solid. Intermediate 2G. was used in the next step without further purification. LCMS Anal. Calc'd for C24H23F6N5O3 543.46, found [M+H] 543.9.
Aufarbeitung
- customat rt
- customovernight
- filtrationThe reaction was filtered
- washsolids were rinsed with THF
- additionThe filtrate was diluted with EtOAc (40 mL)
- washwashed with sat'd Na2CO3
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-ee86fc6a067d4bb5af4ffcb248898c30
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08791091B2
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