Acetic Acid → HCID 86660597, compound

HRID 2367951Notes

Reaction equation

HRID 2367951 reaction equation
[CH2:1]([C:4]([C@:6](C(=O)C1C=CC=CC=1)([C@@:8](C(=O)C1C=CC=CC=1)([C@@H:10]([N:13]=[N+:14]=[N-:15])[CH2:11][OH:12])[OH:9])[OH:7])=[O:5])[CH:2]=[CH2:3].C1COCC1.C[O-].[Na+].C(O)(=O)C>CO>[CH2:1]([C:4]([C@H:6]([C@@H:8]([C@@H:10]([N:13]=[N+:14]=[N-:15])[CH2:11][OH:12])[OH:9])[OH:7])=[O:5])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 86660598HCID 86660598, compound

Product 1

HCID 86660597HCID 86660597, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-allyl-2,3-dibenzoyl-4-azido-4-deoxy-L-xylose 35 (12.0 g, 28.3 mmol) was dissolved in 5:1 methanol:THF (70 mL); to this solution was added sodium methoxide (650 μL of 25% solution, 2.83 mmol). The solution was stirred for 5 h, then to it was added acetic acid (175 μL, 3.11 mmol) and the reaction stirred for 1 min. The solvent was removed in vacuo to give 36 as a thick oil. The material was used without further purification.

Workup

  1. stirringthe reaction stirred for 1 min
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f2905d5d694c44d8bd212b876e00bbd8
Source dataset
uspto-grants-2014_04
Patent number
US08703723B2

Reaction notes

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