反応 #2063678

反応方程式

hydroxylamine hydrochloride

sodium bicarbonate

oxalyl chloride

1-benzoyl-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid

→

gum

収率 103.4%

1-Benzoyl-4-{[4(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1,4-diazepane-5-carboxamide

収率 103.4%

溶媒

tetrahydrofuran

water

Ethyl acetate

dichloromethane

dichloromethane

dimethylformamide

triethylamine

dimethylformamide

反応条件

後処理

1. 1
   その他the resulting reaction mixture
2. 2
   その他to warn to room temperature
3. 3
   workup.STIRRINGstirred for another 18h
4. 4
   洗浄was washed with aqueous sodium bicarbonate (3×)
5. 5
   乾燥dried over anhydrous potassium carbonate
6. 6
   濃縮Concentration in vacuo

実験手順

To oxalyl chloride (0.72 mL of a 2 M solution in dichloromethane) in dichloromethane (1 mL) at 0° C. was added dimethylformamide (0.11 mL). After 15 min a solution of 1-benzoyl-4-{[4-(2-butynyloxy)phenyl]sulfonyl}-1,4-diazepane-5-carboxylic acid (0.328 g, 0.718 mmol) in dimethylformamide was added and the resulting reaction mixture was stirred at room temperature for 1h In a separate flask, 1.5 mL of triethylamine was added to a 0° C. mixture of 0.50 g of hydroxylamine hydrochloride in 15.4 mL of tetrahydrofuran and 3.8 mL of water. After this mixture stirred for 15 min at 0° C., the acid chloride solution was added to it in one portion and the resulting solution was allowed to warn to room temperature and stirred for another 18h. Ethyl acetate and aqueous sodium bicarbonate were then added to the reaction flask The organic phase was washed with aqueous sodium bicarbonate (3×) and dried over anhydrous potassium carbonate. Concentration in vacuo gave a thick gum (0.35 g) which was chromatographed on silica gel eluting with dichloromethane/methanol to give an off-white foam (0.22 g) which was triturated with diethyl ether to give 1-benzoyl-{[4-{[4-(2-butynyloxy)phenyl]sulfonyl}-N-hydroxy-1,4-diazepane-5-carboxamide as an off white powder (0.173 g). Electrospray Mass Spec 472.3(M+H)+.

出典