Hydrochloric Acid → HCID 86602939, compound

HRID 549471Notes

Reaction equation

HRID 549471 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([OH:25])[C@@H:14]([CH2:26][O:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:45](Cl)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:45]([O:25][C@@H:15]1[C@@H:14]([CH2:26][O:27][S:28]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:16]1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10029893HCID 10029893, compound

Product 1

HCID 86602939HCID 86602939, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2,3-di-O-Benzyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside (J. Org. Chem., 2001, 66, 5965-5975) (163.9 g, 310 mmol) was dissolved in methylene chloride (1.5 L), 4-dimethylaminopyridine (43.5 g, 352 mmol) and triethylamine (49.0 mL, 352 mmol) were added thereto and benzoyl chloride (43.2 mL, 372 mmol) was added dropwise thereto under ice-cooling, followed by stirring of the mixture at 0° C. for 1 hour. Diluted hydrochloric acid (2N, 500 mL) was added to the reaction mixture and after the mixture was extracted with methylene chloride (1 L), the organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (1 L) and a saturated aqueous NaCl solution (1 L). After it was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1:1, V/V) to obtain the desired title compound (196 g, yield: 99%) as a colorless solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionafter the mixture was extracted with methylene chloride (1 L)
  3. washthe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution (1 L)
  4. dry with materialAfter it was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-81f8192713a246d9af7ccfcdb26975dc
Source dataset
uspto-grants-2011_05
Patent number
US07943584B2

Reaction notes

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