Acetic Acid → HCID 86725165, compound

HRID 592118Notes

Reaction equation

CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(O)(=O)C.[C:23]([O:31][C@@H:32]1[C@@H:49]([O:50][Si](C(C)(C)C)(C)C)[C@H:48]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[O:46][C@H:33]1[S:34][C:35]1[CH:40]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH:38]=[CH:37][C:36]=1[CH3:45])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[C:23]([O:31][C@@H:32]1[C@@H:49]([OH:50])[C@H:48]([O:58][CH2:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[C@@H:47]([CH2:66][O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[O:46][C@H:33]1[S:34][C:35]1[CH:40]=[C:39]([C:41]([CH3:43])([CH3:44])[CH3:42])[CH:38]=[CH:37][C:36]=1[CH3:45])(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of TBAF.3H2O (1.10 g, 3.48 mmol) and acetic acid (266 μl, 4.64 mmol) in DMF (4 ml) was added to a solution of 29 (430 mg, 0.58 mmol) in DMF (4 ml). The mixture was stirred for 3 days at 35° C. After dilution with Et2O the phases were separated and the organic phase washed with a 0.1 M HCl solution, saturated aqueous NaHCO3 solution and brine. The organic phase was then dried over MgSO4, filtered and concentrated. The product 40 was taken directly to the next step.

Workup

customAfter dilution with Et2O the phases were separated
washthe organic phase washed with a 0.1 M HCl solution, saturated aqueous NaHCO3 solution and brine
dry with materialThe organic phase was then dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2d8ec54f13ac4cd38969ddd422e60a37
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238669B2

Reaction notes

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