Acetic Acid → GS-5759

HRID 1944976Notes

Reaction equation

HRID 1944976 reaction equation
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

Participants

5

Reactant 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

Product 1

HCID 53495160GS-5759

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-acc2939c1f744ee5a5e94a7d94cff597
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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