Water → HCID 21269061, compound

HRID 1195059Notes

Reaction equation

HRID 1195059 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][CH2:16][N:17]=[N+:18]=[N-:19])/[C:8]([O:10]CC)=[O:9])[N:6]=1.O>CO.[OH-].[Na+]>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][CH2:16][N:17]=[N+:18]=[N-:19])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 962WaterHCID 140352896HCID 140352896, compound

Product 1

HCID 21269061HCID 21269061, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

8.1 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(2-azidoethoxy)imino]-acetate are dissolved in 150 ml of methanol and 45 ml of 2N aqueous sodium hydroxide solution. After 20 hours, 50 ml of water are added thereto. The methanol is then removed in vacuo. The aqueous solution is treated with 90 ml of 1N aqueous hydrochloric acid and concentrated to dryness. The residue is taken up in 200 ml of dimethylformamide. The sodium chloride is removed by filtration and the solution is concentrated to 50 ml. The acid is precipitated by the addition of acetonitrile. There are obtained 6.5 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-(2-azidoethoxy)imino]-acetic acid. Yield: 6.5 g of melting point 180° C.

Workup

  1. customThe methanol is then removed in vacuo
  2. additionThe aqueous solution is treated with 90 ml of 1N aqueous hydrochloric acid
  3. concentrationconcentrated to dryness
  4. customThe sodium chloride is removed by filtration
  5. concentrationthe solution is concentrated to 50 ml
  6. customThe acid is precipitated by the addition of acetonitrile

Sources & evidence

ORD record
ord-530fbcda2f96444b986f88a5f1731b06
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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