Trifluoroacetic acid → HCID 45279959, Verbindung

HRID 218013

Reaktionsgleichung

Reaktionsgleichung von HRID 218013
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1)#[N:2].C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:54][C:55]1[CH:56]=[C:57]([C@@:66]23[N:75]=[C:74]([NH:76]C(=O)OC(C)(C)C)[S:73][CH2:72][C@@H:71]2[CH2:70][CH2:69][O:68][CH2:67]3)[C:58]2[O:62][C:61]([F:64])([F:63])[O:60][C:59]=2[CH:65]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>ClCCl.O>[NH2:76][C:74]1[S:73][CH2:72][C@H:71]2[C@:66]([C:57]3[C:58]4[O:62][C:61]([F:64])([F:63])[O:60][C:59]=4[CH:65]=[C:55]([NH:54][C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=4)=[O:11])[CH:56]=3)([CH2:67][O:68][CH2:69][CH2:70]2)[N:75]=1

Komponenten

9

Edukt 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 124007345-Cyanopyridine-2-carboxylic acidHCID 59281180tert-butyl (+/-)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

Produkt 1

HCID 45279959HCID 45279959, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5-Cyanopyridine-2-carboxylic acid (4.0 mg), diisopropylethylamine (11.5 μl) and PyBOP (17.6 mg) were added to a solution of tert-butyl (±)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (10 mg) in dichloromethane (2.0 ml) in an ice bath. The mixture was heated to room temperature and stirred for four hours. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain an intermediate. The resulting intermediate was dissolved in dichloromethane (3.0 ml) and TFA (1.0 ml) was added. After stirring at room temperature for four hours, the reaction solution was diluted with water and neutralized with a sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain the title compound.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by NH-pTLC
  3. customto obtain an intermediate
  4. stirringAfter stirring at room temperature for four hours
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by NH-pTLC

Quellen und Nachweise

ORD-Eintrag
ord-39bc75924af84a62a8b718f43cc4731a
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198269B2

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