Trifluoroacetic anhydride → HCID 21866452, compound

HRID 1582914Notes

Reaction equation

[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([C:19]([NH2:21])=O)=[C:13]([C:15]([F:18])([F:17])[F:16])[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:19]#[N:21])=[C:13]([C:15]([F:17])([F:18])[F:16])[N:14]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

Conditions

Temperature: -5 °C

Procedure

2-(N-BOC-Aminomethyl)-4-trifluoromethylthiazole-5-carboxamide [sic] (4.6 g, 14.14 mmol) was dissolved in dichloromethane (30 ml) and cooled to −5° C. Ethyldiisopropylamine (4.6 g, 35.35 mmol) and a solution of trifluoroacetic anhydride (3.4 g, 16.26 mmol) in dichloromethane (10 ml) were added at this temperature. Then, the mixture was stirred for a further 2 hours at 0° C. It was washed in succession with saturated sodium hydrogen carbonate solution and 5% strength citric acid solution. After drying (MgSO4), the solvent was removed on a rotary evaporator. The crude product was extracted by stirring with diethyl ether/petroleum ether. The supernatant was separated from the oil and concentrated on a rotary evaporator. Yield: 1.9 g (6.18 mmol, 44%).

Workup

washIt was washed in succession with saturated sodium hydrogen carbonate solution and 5% strength citric acid solution
dry with materialAfter drying (MgSO4)
customthe solvent was removed on a rotary evaporator
extractionThe crude product was extracted
stirringby stirring with diethyl ether/petroleum ether
customThe supernatant was separated from the oil
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-3f02e585a58c421f9a9a244f05bada6a
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06740647B1

Reaction notes

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