Sodium Bicarbonate → HCID 70377649, compound

HRID 2351542Notes

Reaction equation

HRID 2351542 reaction equation
[CH3:1][C:2]1[O:10][C@@H:9]2[C@@H:4]([C@@H:5]([O:20][C:21]([CH3:23])=[O:22])[C@H:6]([O:16][C:17]([CH3:19])=[O:18])[C@@H:7]([CH2:11][O:12][C:13]([CH3:15])=[O:14])[O:8]2)[N:3]=1.[CH2:24]([O:31][C:32](=[O:35])[CH2:33][OH:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[CH2:24]([O:31][C:32](=[O:35])[CH2:33][O:34][C@@H:9]1[O:8][C@H:7]([CH2:11][O:12][C:13](=[O:14])[CH3:15])[C@@H:6]([O:16][C:17](=[O:18])[CH3:19])[C@H:5]([O:20][C:21](=[O:22])[CH3:23])[C@H:4]1[NH:3][C:2](=[O:10])[CH3:1])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 561337Benzyl 2-hydroxyacetateHCID 9883925(3aR,5R,6S,7R,7aR)-5-[(Acetyloxy)methyl]-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]oxazole-6,7-diyl diacetate

Product 1

HCID 70377649HCID 70377649, compound

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 600 mg (1.82 mmol) of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline of the formula ##STR13## [prepared according to V. K. Srivastava, Carbohydrate Research 103, 286 (1982)]and 605 mg (3.64 mmol) of glycolic acid benzyl ester in 6 ml of methylene chloride is added to a solution of 300 mg (1.85 mmol) of iron(III) chloride (anhydrous) in 6 ml of absolute methylene chloride and the whole is stirred for 21 hours at 22°. 8 ml of cold, saturated sodium bicarbonate solution are added and the mixture is diluted with 100 ml of chloroform and filtered until clear. The organic phase of the filtrate yields, after drying over magnesium sulphate and concentration by evaporation, a yellow oil which is purified by digesting an ethyl acetate solution with hexane and by chromatography on silica gel. 2-(2-acetylamino-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)-acetic acid benzyl ester is obtained in the form of a colourless powder.

Workup

  1. filtrationfiltered until clear
  2. customThe organic phase of the filtrate yields
  3. dry with materialafter drying over magnesium sulphate and concentration by evaporation
  4. customa yellow oil which is purified

Sources & evidence

ORD record
ord-5668df1214f0467a9a3e8562f2e29e34
Source dataset
uspto-grants-1989_10
Patent number
US04873322

Reaction notes

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