Water → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-methyltetrazol-5-yl)methoxyimino]acetic acid

HRID 1195067Notes

Reaction equation

HRID 1195067 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]2[N:20]([CH3:21])[N:19]=[N:18][N:17]=2)/[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].O>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]2[N:20]([CH3:21])[N:19]=[N:18][N:17]=2)/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21269052HCID 21269052, compound

Product 1

HCID 88629951(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-methyltetrazol-5-yl)methoxyimino]acetic acidYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

24.9 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-methyl-1H-tetrazol-5-yl)methoxy]imino]-acetate are dissolved in 100 ml of methanol and the solution is treated with 250 ml of 1N aqueous sodium hydroxide solution. The mixture is stirred at room temperature for 12 hours and treated with 150 ml of water. The methanol is subsequently removed under reduced pressure. The aqueous solution is washed with ethyl acetate and treated with 250 ml of 1N aqueous hydrochloric acid. The acid crystallizes upon concentration. The acid is filtered off and, for the removal of water (about 16%), stirred for 6 hours in 350 ml of acetonitrile, filtered and dried. There are obtained 14.2 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-methyl-1H-tetrazol-5-yl)methoxy]imino]-acetic acid of melting point 185° C.

Workup

  1. customThe methanol is subsequently removed under reduced pressure
  2. washThe aqueous solution is washed with ethyl acetate
  3. additiontreated with 250 ml of 1N aqueous hydrochloric acid
  4. customThe acid crystallizes upon concentration
  5. filtrationThe acid is filtered off and, for the removal of water (about 16%)
  6. stirringstirred for 6 hours in 350 ml of acetonitrile
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-9ed51f4e68804a0f92582264bb90e599
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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