Acetic Anhydride → HCID 70583977, compound

HRID 1706839Notes

Reaction equation

HRID 1706839 reaction equation
[N:1]([CH2:4][C@H:5]1[O:12][C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][C@@H:6]1[OH:13])=[N+]=[N-].[C:14](OC(=O)C)(=[O:16])[CH3:15]>CO.[Pd]>[C:14]([NH:1][CH2:4][C@H:5]1[O:12][C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][C@@H:6]1[OH:13])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86737059HCID 86737059, compound

Product 1

HCID 70583977HCID 70583977, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 6-azido-2,3,6-trideoxy-α-D-erythro-hexopyranoside (3.0 g, 16 mmol) in methanol (100 ml) containing acetic anhydride (2 ml) was hydrogenated over 10% palladium-on-charcoal (0.4 g) at room temperature under a pressure of 2.5 atms. for 5 h. The catalyst was filtered off and the filtrate was evaporated to dryness giving a syrupy residue which crystallized upon treatement with ether to yield 3.18 g, 98%. The product was recrystallized from chloroform-ether to give pure methyl 6-acetamido-2,3,6-trideoxy-α-D-erythro-hexopyranoside. M.p.: 117°-118°. [α]546121 -13° (c 1, chloroform).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customgiving a syrupy residue which
  4. customcrystallized upon treatement with ether
  5. customto yield 3.18 g, 98%
  6. customThe product was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-cda4daa1538b45058ddfde6f8d4465e8
Source dataset
uspto-grants-1980_06
Patent number
US04208531

Reaction notes

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