Dimethylformamide → HCID 86638442, compound

HRID 1009875Notes

Reaction equation

CN(C)C=O.[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][C:53]=2[CH3:59])[C:48]([CH3:60])=[CH:47][C:46]=1[O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:70][CH2:71][N:72]1[C:76](=[O:77])[C:75]2=[CH:78][CH:79]=[CH:80][CH:81]=[C:74]2[C:73]1=[O:82].C(=O)([O-])[O-].[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O>[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:70][CH2:71][N:72]3[C:73](=[O:82])[C:74]4[C:75](=[CH:78][CH:79]=[CH:80][CH:81]=4)[C:76]3=[O:77])=[CH:54][C:53]=2[CH3:59])[C:48]([CH3:60])=[CH:47][C:46]=1[O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a N,N-dimethylformamide solution (5.0 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-hydroxy-2-methylbenzyl)-4-methylphenyl]-D-glucitol (340 mg, 0.40 mmol) and N-(2-bromoethyl)phthalimide (1.02 g, 4.0 mmol) were added potassium carbonate (553 mg, 4.0 mmol) and n-Bu4NI (14 mg, 0.038 mmol). The reaction mixture was stirred at 80° C. for 3.5 hours. After the mixture was cooled to room temperature, water was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain the title compound (60 mg, 15%) as a pale yellow oily compound.

Workup

temperatureAfter the mixture was cooled to room temperature
extractionthe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried with anhydrous magnesium sulfate
filtrationThe drying agent was filtered off
customthe solvent was evaporated under reduced pressure
customto obtain a residue
customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-5f875fb6dab8495dbcfe03cddd2d0e46
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973012B2

Reaction notes

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