Acetic Anhydride → HCID 19809511, compound

HRID 374261Notes

Reaction equation

HRID 374261 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:7]23[CH2:14][N:11]([CH2:12][CH2:13]2)[CH2:10][CH2:9][CH2:8]3)=[CH:5][N:6]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([NH:1][C:2]1[O:3][C:4]([C:7]23[CH2:14][N:11]([CH2:12][CH2:13]2)[CH2:10][CH2:9][CH2:8]3)=[CH:5][N:6]=1)(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 19809499HCID 19809499, compound

Product 1

HCID 19809511HCID 19809511, compoundYield 60%

Procedure

A solution of (±)5-(2-amino-1,3-oxazol-5-yl)-1-azabicyclo[3.2.1]octane (E3) (0.25g, 1.3 mmole) in acetic anhydride (8 ml) was refluxed for 1h under nitrogen. The reaction mixture was concentrated in vacuo and the residue treated with saturated aqueous potassium carbonate solution (10 ml). After extraction into chloroform (3×10 ml) the organic extracts were dried over sodium sulphate and concentrated in vacuo. Trituration of the resulting gum with ether afforded the title compound (E14) as a solid (180 mg, 60%) m.p. 142°-143° C. (from methanol-ether).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with saturated aqueous potassium carbonate solution (10 ml)
  3. extractionAfter extraction into chloroform (3×10 ml) the organic extracts
  4. dry with materialwere dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe7e96758f6546b685272ae6419076db
Source dataset
uspto-grants-1992_11
Patent number
US05166357

Reaction notes

Loading…