Trifluoroacetic anhydride → HCID 21866550, compound

HRID 1582910Notes

Reaction equation

HRID 1582910 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH3:18])=[C:13]([C:15]([NH2:17])=O)[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)CC)(C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:15]([C:13]1[N:14]=[C:10]([CH2:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[S:11][C:12]=1[CH3:18])#[N:17]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 21866542HCID 21866542, compound

Product 1

HCID 21866550HCID 21866550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2-(N-Boc-Aminomethyl)-5-methylthiazole-4-carboxamide (6.8 g, 25 mmol) was introduced into dichloromethane (120 ml). After the mixture had cooled to 0° C. diisopropylethylamine (15.84 g, 122.8 mmol) was added dropwise. Then, a solution of trifluoroacetic anhydride (8.25 g, 39.3 mmol) in dichloromethane (20 ml) was added dropwise at −5° C. in the course of 30 minutes. After the mixture had been stirred for 30 minutes at 0° C., it was warmed to room temperature, and stirring was continued for another 12 hours. The mixture was diluted with dichloromethane (100 ml) and washed with 20% strength citric acid, saturated NaHCO3 [sic] solution and saturated NaCl solution. The organic phase was dried (MgSO4) and concentrated in vacuo. Yield: 6.3 g (25 mmol, quant.).

Workup

  1. additionwas added dropwise
  2. temperatureit was warmed to room temperature
  3. stirringstirring
  4. waitwas continued for another 12 hours
  5. washwashed with 20% strength citric acid, saturated NaHCO3 [sic] solution and saturated NaCl solution
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41a4d550e4df43d08e160e4a5442a75f
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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