Potassium Carbonate → HCID 10231749, compound

HRID 2307745Notes

Reaction equation

HRID 2307745 reaction equation
[C:1]([O:7][C@H:8]1[C@@H:14]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:13]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C@@H:12]([CH2:29][O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[O:11][CH:9]1[OH:10])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].C([O:50][C:51](=[O:54])[CH2:52]Br)C1C=CC=CC=1.COC(C)(C)C>[Cl-].C[N+](C)(C)C.COCCOCCOC>[C:1]([O:7][C@H:8]1[C@@H:14]([O:15][C:16](=[O:21])[C:17]([CH3:18])([CH3:20])[CH3:19])[C@H:13]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C@@H:12]([CH2:29][O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[O:11][CH:9]1[O:10][CH2:52][C:51]([OH:54])=[O:50])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 62576Benzyl bromoacetateHCID 12997455HCID 12997455, compound

Product 1

HCID 10231749HCID 10231749, compound

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 8150DiglymeSolvent

Conditions

Temperature
10 °C

Procedure

A mixture that consists of 51.66 g (100 mmol) of 2,3,4,6-tetra-O-pivaloyl-mannopyranose, 0.55 g (5 mmol) of tetramethylammonium chloride and 82.93 g (600 mmol) of fine-powder potassium carbonate in 350 ml of diethylene glycol dimethyl ether is cooled to 10° C. At 10° C., 36.65 g (160 mmol) of 2-bromoacetic acid benzyl ester is added in drops within 10 minutes while being stirred vigorously. It is stirred for two hours at 10° 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, mixed with 5 g of palladium (10%) on activated carbon and hydrogenated until hydrogen absorption is completed. Catalyst is filtered out, it is rewashed with ethanol, and the combined solutions are evaporated to the dry state in a vacuum. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5). The product-containing fractions are concentrated by evaporation, dissolved in 400 ml of ethyl acetate and shaken out three times with 200 ml of water. Then, the organic phase is separated and evaporated to the dry state in a vacuum.

Workup

  1. stirringIt is stirred for two hours at 10° C
  2. filtrationsolid is filtered out
  3. customthe filtrate is evaporated to the dry state in a vacuum
  4. additionmixed with 5 g of palladium (10%) on activated carbon and hydrogenated until hydrogen absorption
  5. filtrationCatalyst is filtered out
  6. customthe combined solutions are evaporated to the dry state in a vacuum
  7. customThe residue is chromatographed on silica gel (mobile solvent: dichloromethane/n=hexane/ethanol/acetic acid=20:5:3:0.5)
  8. concentrationThe product-containing fractions are concentrated by evaporation
  9. dissolutiondissolved in 400 ml of ethyl acetate
  10. stirringshaken out three times with 200 ml of water
  11. customThen, the organic phase is separated
  12. customevaporated to the dry state in a vacuum

Sources & evidence

ORD record
ord-b4af431218f94c33ab3f36dbd8e75b49
Source dataset
uspto-grants-2004_12
Patent number
US06831164B2

Reaction notes

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