Trifluoroacetic acid → N-(2,4-dichloro-thiazol-5-yl)-3-methylsulfanyl-propionamide

HRID 2199231Notes

Reaction equation

HRID 2199231 reaction equation
C(OC(=O)[N:7]([C:14]1[S:18][C:17]([Cl:19])=[N:16][C:15]=1[Cl:20])[C:8](=[O:13])[CH2:9][CH2:10][S:11][CH3:12])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:19][C:17]1[S:18][C:14]([NH:7][C:8](=[O:13])[CH2:9][CH2:10][S:11][CH3:12])=[C:15]([Cl:20])[N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59580673HCID 59580673, compound

Product 1

HCID 59580948N-(2,4-dichloro-thiazol-5-yl)-3-methylsulfanyl-propionamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2,4-dichloro-thiazol-5-yl)-(3-methylsulfanyl-propionyl)-carbamic acid tert-butyl ester (1.10 g, 2.97 mmol) in DCM (10 mL) was added trifluoroacetic acid (3.4 g, 2.2 mL, 30 mmol). The solution was stirred at room temperature for 15 minutes, before it was quenched slowly with saturated NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with 20 mL DCM. The combined organic layer was dried over Na2SO4 and purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give product as a white solid (612 mg, 76%): 1H NMR (300 MHz, CDCl3) δ 8.79 (s, 1H), 2.90 (t, J=7.2 Hz, 2H), 2.79 (t, J=7.2 Hz, 2H), 2.29 (s, 3H); ESIMS m/z 271.0 (M+1).

Workup

  1. customwas quenched slowly with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 20 mL DCM
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. custompurified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ced095539898454f8cb3d5c03bfb2450
Source dataset
uspto-grants-2016_06
Patent number
US09357780B2

Reaction notes

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