Water → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-oxo-2-piperidin-1-ylethoxy)iminoacetic acid

HRID 1195063Notes

Reaction equation

HRID 1195063 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])/[C:8]([O:10]CC)=[O:9])[N:6]=1.O.[OH-].[Na+]>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21269051HCID 21269051, compound

Product 1

HCID 88630264(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-oxo-2-piperidin-1-ylethoxy)iminoacetic acidYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

77.2 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-piperidinecarbonyl)methoxy]imino]-acetate are dissolved in 3 l of methanol and 265 ml of water and the solution is treated with 250 ml of 1N aqueous sodium hydroxide solution. The saponification is complete after 48 hours. 500 ml of water are added thereto and the methanol is removed under reduced pressure. The aqueous solution is washed with ethyl acetate, treated with 250 ml of 1N aqueous hydrochloric acid and concentrated to half of the volume. The acid which crystallizes out is filtered off and dried. There are obtained 55.3 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-[(1-piperidinecarbonyl)methoxy]imino]-acetic acid of melting point 177° C.

Workup

  1. customthe methanol is removed under reduced pressure
  2. washThe aqueous solution is washed with ethyl acetate
  3. additiontreated with 250 ml of 1N aqueous hydrochloric acid
  4. concentrationconcentrated to half of the volume
  5. customThe acid which crystallizes out
  6. filtrationis filtered off
  7. customdried

Sources & evidence

ORD record
ord-a40ea4be599f4537b6f2be845c970e9f
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

Loading…