Water → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-(azepan-1-yl)-2-oxoethoxy]iminoacetic acid

HRID 1195065Notes

Reaction equation

HRID 1195065 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[CH2:24][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[CH2:24][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 962WaterHCID 14798Sodium HydroxideHCID 21269047HCID 21269047, compound

Product 1

HCID 88630288(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-(azepan-1-yl)-2-oxoethoxy]iminoacetic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

68 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[[(hexahydro-1H-azepin-1-yl)carbonyl]methoxy]imino]-acetate are dissolved in 2.5 l of methanol and 250 ml of water and the solution is treated with 220 ml of 1N aqueous sodium hydroxide solution. The methanol is removed under reduced pressure after 48 hours. The aqueous solution is washed with ethyl acetate and treated with 220 ml of 1N aqueous hydrochloric acid. The acid which crystallizes out is filtered off and dried. There are obtained 51 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-[[(hexahydro-1H-azepin-1-yl)carbonyl]methoxy]imino]-acetic acid of melting point 178°-179° C.

Workup

  1. customThe methanol is removed under reduced pressure after 48 hours
  2. washThe aqueous solution is washed with ethyl acetate
  3. additiontreated with 220 ml of 1N aqueous hydrochloric acid
  4. customThe acid which crystallizes out
  5. filtrationis filtered off
  6. customdried

Sources & evidence

ORD record
ord-ec0d942ebb694dd8b944512ed5b5e023
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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