Water → methyl 5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

HRID 882331

Reaction equation

HRID 882331 reaction equation
[C:1]([NH:4][CH:5]1[CH:10]([CH:11]([O:22][C:23](=[O:25])[CH3:24])[CH:12]([O:18][C:19](=[O:21])[CH3:20])[CH2:13][O:14][C:15](=[O:17])[CH3:16])[O:9][C:8]([C:26]([O:28][CH3:29])=[O:27])=[CH:7][CH:6]1[N:30]=[N+]=[N-])(=[O:3])[CH3:2].O.[Cl-].[NH4+]>C(Cl)Cl.[Zn]>[C:1]([NH:4][CH:5]1[CH:10]([CH:11]([O:22][C:23](=[O:25])[CH3:24])[CH:12]([O:18][C:19](=[O:21])[CH3:20])[CH2:13][O:14][C:15](=[O:17])[CH3:16])[O:9][C:8]([C:26]([O:28][CH3:29])=[O:27])=[CH:7][CH:6]1[NH2:30])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 14802589methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

Product 1

HCID 67367461methyl 5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylateYield 100.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a reaction vessel, 55 g of methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate, 500 ml of denatured alcohol and 100 ml of water was added under stirring at room temperature. To the reaction mass 14 g ammonium chloride and 18 g zinc dust was added. The reaction mixture was stirred at 20° C.-30° C. for 30 minutes. On completion of reaction, the reaction mass was cooled to 10° C. and then filtered through hyflo. The filtrate was concentrated under vacuum to obtain a solid product which was then dissolved in about 200 ml of methylene dichloride. The organic layer was filtered and concentrated to yield 52 g of solid title compound, dried under vacuum (yield—94%, HPLC purity—96%).

Workup

  1. stirringThe reaction mixture was stirred at 20° C.-30° C. for 30 minutes
  2. customOn completion of reaction
  3. temperaturethe reaction mass was cooled to 10° C.
  4. filtrationfiltered through hyflo
  5. concentrationThe filtrate was concentrated under vacuum
  6. customto obtain a solid product which
  7. filtrationThe organic layer was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-89ce5d234f184d72b72737f740fc907e
Source dataset
uspto-grants-2015_03
Patent number
US08993789B2

Linked notes

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