Trifluoroacetic anhydride → HCID 21866517, compound

HRID 1582911Notes

Reaction equation

HRID 1582911 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:16]([NH2:18])=O)=[C:13]([CH3:15])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(C(C)C)C(C)C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:16]#[N:18])=[C:13]([CH3:15])[N:14]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 21866488Carbamic acid, [[5-(aminocarbonyl)-4-methyl-2-thiazolyl]methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 21866517HCID 21866517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

2-(N-BOC-Aminomethyl)-4-methylthiazole-5-carboxamide [sic] (11.13 g, 41.02 mmol) was suspended in dichloromethane (75 ml) and cooled to 0° C. At this temperature, ethyldiisopropylamine (17.86 ml, 102.55 mmol) was first added, and then, slowly, a solution of trifluoroacetic anhydride (6.56 ml, 47.17 mmol) in dichloromethane (20 ml). After stirring for 1 hour, the mixture was diluted with dichloromethane and washed with 5% strength citric acid solution. After drying (MgSO4), the solvent was removed on a rotary evaporator and the crude product was purified by flash chromatography.

Workup

  1. washwashed with 5% strength citric acid solution
  2. dry with materialAfter drying (MgSO4)
  3. customthe solvent was removed on a rotary evaporator
  4. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e3233e3658a647299ea0e7f30be7437b
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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