Anisole → (Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid

HRID 1031207Notes

Reaction equation

HRID 1031207 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([O:18]C(C)(C)C)=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 13577059(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-methyl-1-((2-methylpropan-2-yl)oxy)-1-oxopropan-2-yl)oxyiminoacetic acid

Product 1

HCID 15077653(Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetic acid (17.8 g) and anisole (18 ml) in trifluoroacetic acid (36 ml) was stirred for 4.0 hours at room temperature. The reaction mixture was concentrated under reduced pressure and an aqueous solution of sodium bicarbonate was added thereto to adjust to pH 6.0. The aqueous solution was washed with ethyl acetate, adjusted to pH 3.8 with 6N hydrochloric acid and washed with ethyl acetate. The aqueous layer was separated and 6N hydrochloric acid was added thereto to adjust to pH 1.0. After the mixture was stirred for 10 minutes, the resultant precipitate was collected by filtration to give (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetic acid (13.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous solution of sodium bicarbonate was added
  3. washThe aqueous solution was washed with ethyl acetate
  4. washwashed with ethyl acetate
  5. customThe aqueous layer was separated
  6. addition6N hydrochloric acid was added
  7. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-2a8631dde28340aebda15b4881367c39
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

Loading…