Acetic Acid → (R)-6-[[3-[[8-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944975Notes

Reaction equation

HRID 1944975 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C@H:27]([C:73]1[CH:82]=[CH:81][C:80]([OH:83])=[C:79]2[C:74]=1[CH:75]=[CH:76][C:77](=[O:84])[NH:78]2)[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([C:41]1[CH:42]=[C:43]([S:47]([C:50]2[CH:51]=[C:52]3[C:57](=[C:58]([CH3:60])[CH:59]=2)[N:56]=[CH:55][C:54]([C:61]([NH2:63])=[O:62])=[C:53]3[NH:64][C:65]2[CH:70]=[CH:69][CH:68]=[C:67]([O:71][CH3:72])[CH:66]=2)(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1)=[O:40])(C(C)(C)C)(C)C.C(O)(=O)C>C1COCC1>[OH:26][C@H:27]([C:73]1[CH:82]=[CH:81][C:80]([OH:83])=[C:79]2[C:74]=1[CH:75]=[CH:76][C:77](=[O:84])[NH:78]2)[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([C:41]1[CH:42]=[C:43]([S:47]([C:50]2[CH:51]=[C:52]3[C:57](=[C:58]([CH3:60])[CH:59]=2)[N:56]=[CH:55][C:54]([C:61]([NH2:63])=[O:62])=[C:53]3[NH:64][C:65]2[CH:70]=[CH:69][CH:68]=[C:67]([O:71][CH3:72])[CH:66]=2)(=[O:48])=[O:49])[CH:44]=[CH:45][CH:46]=1)=[O:40]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 86659116(R)-6-[[3-[[8-[[2-[(tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl]ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 54588137(R)-6-[[3-[[8-[[2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamideYield 28.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of TBAF (1.0 M in THF, 0.244 mL, 0.244 mmol) was added to a stirring solution of Intermediate 148 (76 mg, 0.0813 mmol) in THF (2 mL) at rt. After stirring over night, glacial acetic acid (0.023 mL, 0.407 mmol) was added and stirred for an additional 16 h. The reaction mixture was concentrated and purified by PREP-HPLC to give the title compound (19 mg).

Workup

  1. stirringstirred for an additional 16 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by PREP-HPLC

Sources & evidence

ORD record
ord-7529d12907a94d68b063a7911ae51904
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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