Potassium Carbonate → HCID 10272690, compound

HRID 2307734Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C([O:38][C:39](=[O:42])[CH2:40]Br)C1C=CC=CC=1.COC(C)(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[C:1]([O:4][C@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][CH:6]1[O:7][CH2:40][C:39]([OH:42])=[O:38])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture that consists of 34.83 g (100 mmol) of 2,3,4,6-tetra-O-acetyl-mannopyranose, 1.70 g (5 mmol) of tetrabutylammonium hydrogen sulfate and 82.93 g (600 mmol) of fine-powder potassium carbonate in 350 ml of dioxane is cooled to 0° C. At 0° C., 34.36 g (150 mmol) of bromoacetic acid benzyl ester is added in drops over 10 minutes while being stirred vigorously. It is stirred for one hour at 0° C. 250 ml of MTB (methyl-tert-butyl ether) is added, solid is filtered out, and the filtrate is evaporated to the dry state in a vacuum. The residue is taken up in 500 ml of ethanol. 5 g of palladium (10%) on activated carbon is added thereto and hydrogenated until no more hydrogen is taken up by the solution. Catalyst is filtered out, it is rewashed with ethanol, and the combined solutions are evaporated to the dry state in a vacuum.

Workup

stirringIt is stirred for one hour at 0° C
filtrationsolid is filtered out
customthe filtrate is evaporated to the dry state in a vacuum
addition5 g of palladium (10%) on activated carbon is added
filtrationCatalyst is filtered out
customthe combined solutions are evaporated to the dry state in a vacuum

Sources & evidence

ORD record: ord-a4e7ed4d94624b7cb647fe21af629e3d
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06831164B2

Reaction notes

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