Acetic Acid → GS-5759

HRID 1944976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1944976
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C@H:27]([C:76]1[CH:85]=[CH:84][C:83]([OH:86])=[C:82]2[C:77]=1[CH:78]=[CH:79][C:80](=[O:87])[NH:81]2)[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][C:33]#[C:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42]([C:44]2[CH:45]=[C:46]([S:50]([C:53]3[CH:54]=[C:55]4[C:60](=[C:61]([CH3:63])[CH:62]=3)[N:59]=[CH:58][C:57]([C:64]([NH2:66])=[O:65])=[C:56]4[NH:67][C:68]3[CH:73]=[CH:72][CH:71]=[C:70]([O:74][CH3:75])[CH:69]=3)(=[O:52])=[O:51])[CH:47]=[CH:48][CH:49]=2)=[O:43])=[CH:37][CH:36]=1)(C(C)(C)C)(C)C.C(O)(=O)C>C1COCC1>[OH:26][C@H:27]([C:76]1[CH:85]=[CH:84][C:83]([OH:86])=[C:82]2[C:77]=1[CH:78]=[CH:79][C:80](=[O:87])[NH:81]2)[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][C:33]#[C:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][C:42]([C:44]2[CH:45]=[C:46]([S:50]([C:53]3[CH:54]=[C:55]4[C:60](=[C:61]([CH3:63])[CH:62]=3)[N:59]=[CH:58][C:57]([C:64]([NH2:66])=[O:65])=[C:56]4[NH:67][C:68]3[CH:73]=[CH:72][CH:71]=[C:70]([O:74][CH3:75])[CH:69]=3)(=[O:51])=[O:52])[CH:47]=[CH:48][CH:49]=2)=[O:43])=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 58505204(R)-6-[[3-[[4-[5-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]pent-1-ynyl]-phenyl]carbamoyl]phenyl]-sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Produkt 1

HCID 53495160GS-5759

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBAF (1.0 M) (1.036 mL, 1.036 mmol) was added to a solution of Intermediate 153 (500 mg, 0.518 mmol), and acetic acid (0.5 mL) in THF (15 mL). The solution was stirred overnight at rt. After which time 7N MeOH/NH4 was added to neutralize the acidic mixture. All solvents were removed in vacuo and the resultant solid was suspended in MeOH (30 mL) and filtered. The solid was treated with a mixture of MeOH/water (1:1) (40 mL) and sonicated for 5 min.

Aufarbeitung

  1. customAll solvents were removed in vacuo
  2. filtrationfiltered
  3. additionThe solid was treated with a mixture of MeOH/water (1:1) (40 mL)
  4. customsonicated for 5 min.

Quellen und Nachweise

ORD-Eintrag
ord-acc2939c1f744ee5a5e94a7d94cff597
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394829B2

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