Potassium methyl N-cyanodithioimidocarbonate → 3-(4-Amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester

HRID 1442638Notes

Reaction equation

HRID 1442638 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]([C:12]#[N:13])=[C:8]([OH:11])[CH2:9]Cl)([CH3:4])([CH3:3])[CH3:2].[C:15]([N:17]=[C:18]([S-:21])[S:19][CH3:20])#[N:16].[K+]>CC(C)=O>[C:1]([O:5][C:6](=[O:14])[CH:7]([C:12]#[N:13])[C:8]([C:9]1[S:21][C:18]([S:19][CH3:20])=[N:17][C:15]=1[NH2:16])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2733091Potassium methyl N-cyanodithioimidocarbonateHCID 768375794-Chloro-2-cyano-3-hydroxy-but-2-enoic acid tert-butyl ester

Product 1

HCID 685403423-(4-Amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-chloro-2-cyano-3-hydroxy-but-2-enoic acid tert-butyl ester Compound 1c (51.3 g, 236 mmol) at 0° C. in acetone (750 mL) was added potassium methyl N-cyanodithioimidocarbonate Compound 1e (40.2 g, 236 mmol). After 1 hr the reaction was allowed to warm to RT. The reaction mixture was evaporated down after stirring for 18 hrs. The resulting residue was extracted with ethyl acetate from saturated NaHCO3. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to yield a tan foam, 3-(4-amino-2-methylsulfanyl-thiazol-5-yl)-2-cyano-3-oxo-propionic acid tert-butyl ester Compound 1h, 72.2 g. 1H NMR (CDCl3) δ 4.34 (br s, 2H), 3.14 (br s, 1H), 2.70 (br s, 3H), 1.47 (br s, 9H). MS 314 (MH+).

Workup

  1. customThe reaction mixture was evaporated down
  2. extractionThe resulting residue was extracted with ethyl acetate from saturated NaHCO3
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8aafb594f24d4c63800e65f8ca8aeeb0
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

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