Tetrabutylammonium Fluoride → HCID 68502020, compound

HRID 1176644Notes

Reaction equation

[CH3:1][C:2]1([CH3:56])[O:7][C:6](=[O:8])[N:5](COCC[Si](C)(C)C)[C:4]2[C:17]([CH2:21][O:22][CH:23]3[CH:28]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[O:47][CH3:48])=[CH:31][CH:30]=4)[CH2:27][CH2:26][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:24]3)=[CH:18][CH:19]=[CH:20][C:3]1=2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:1][C:2]1([CH3:56])[O:7][C:6](=[O:8])[NH:5][C:4]2[C:17]([CH2:21][O:22][CH:23]3[CH:28]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=5[O:47][CH3:48])=[CH:31][CH:30]=4)[CH2:27][CH2:26][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:24]3)=[CH:18][CH:19]=[CH:20][C:3]1=2

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 68499729HCID 68499729, compound

Product 1

HCID 68502020HCID 68502020, compound

Procedure

Analogously to Example 228a, 0.45 g of tert-butyl 3-[4,4-dimethyl-2-oxo-1-(2-trimethylsilanylethoxymethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-8-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 4.47 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) are reacted. The title compound is obtained as a yellowish oil. Rf=0.15 (9:1 dichloromethane-methanol); Rt=5.87.

Sources & evidence

ORD record: ord-eb03ae06adc046e387c87f058ac6075f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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