Tetrabutylammonium Fluoride → 6-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[3-(3-hydroxy-propyl)isoxazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

HRID 1096851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096851
[Cl:1][C:2]([Cl:57])([Cl:56])[C:3]([O:6][C:7]([N:9]1[CH:14]2[C:15]([C:34](=[O:48])[N:35]([CH:45]3[CH2:47][CH2:46]3)[CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=3[Cl:44])=[C:16]([C:18]3[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][O:26][Si](C(C)(C)C)(C)C)[CH:19]=3)[CH2:17][CH:10]1[CH2:11][N:12]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:13]2)=[O:8])([CH3:5])[CH3:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[Cl:56][C:2]([Cl:1])([Cl:57])[C:3]([O:6][C:7]([N:9]1[CH:14]2[C:15]([C:34](=[O:48])[N:35]([CH:45]3[CH2:47][CH2:46]3)[CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[C:38]=3[Cl:44])=[C:16]([C:18]3[O:22][N:21]=[C:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH:19]=3)[CH2:17][CH:10]1[CH2:11][N:12]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:13]2)=[O:8])([CH3:4])[CH3:5]

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 866370697-{3-[3-(tert-Butyldimethylsilanyloxy)propyl]isoxazol-5-yl}-6-[cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) ester

Produkt 1

HCID 866370706-[Cyclopropyl-(2,3-dichlorobenzyl)carbamoyl]-7-[3-(3-hydroxy-propyl)isoxazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid 3-tert-butyl ester 9-(2,2,2-trichloro-1,1-dimethylethyl) esterAusbeute 160,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A sol. of compound E5 (728 mg, 0.800 mmol) and TBAF (1.0 M in THF, 1.00 mL, 1.00 mmol) in THF (20 mL) was stirred at 0° C. for 3.5 h. The mixture was diluted with EtOAc and was washed with brine (4×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:4→1:2→1.1→EtOAc) yielded the title compound (1.02 g, 96%). LC-MS: tR=1.17 min, ES+: 795.31.

Aufarbeitung

  1. washwas washed with brine (4×)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (EtOAc/heptane 1:4→1:2→1.1→EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-579807805f2c4002b84442ac4fb71ba1
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138340B2

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