Methanol → 2-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acid

HRID 648405Notes

Reaction equation

HRID 648405 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[C:7]([O:9]CC)=[O:8])[CH2:2][CH3:3].CO.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[C:7]([OH:9])=[O:8])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53867037Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetate

Product 1

HCID 540960402-(2-Amino-4-thiazolyl)-2-propoxyiminoacetic acidYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-n-propoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (10 g.) in a mixture of tetrahydrofuran (39 ml.), methanol (39 ml.) and 1 N sodium hydroxide (75.8 ml.) was stirred at 35° to 40° C. for 5 hours. After the resultant solution was concentrated under reduced pressure, the aqueous residue was adjusted to pH2.5 with 10% hydrochloric acid. The precipitates were collected by filtration and dried to give 2-n-propoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer) (6.2 g.), mp. 161° C. (dec.).

Workup

  1. concentrationAfter the resultant solution was concentrated under reduced pressure
  2. filtrationThe precipitates were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-8441830ec84f401886e663ddfebbb434
Source dataset
uspto-grants-1983_10
Patent number
US04411898

Reaction notes

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