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

HRID 1651158Notes

Reaction equation

HRID 1651158 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-76f2195450894dcea37873ada1112da9
Source dataset
uspto-grants-1990_05
Patent number
US04927818

Reaction notes

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