تفاعل #160199

معادلة التفاعل

Triethylamine

8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecane

4-isopropoxy-3-methyl-benzoic acid

HATU

→

[8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

المردود 79.0%

المذيبات

NaHCO3

DMF

DCM

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with DCM (3×5 mL)
2. 2
   تجفيفdried over MgSO4
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىpurified by silica gel column chromatography (0-100% EtOAc/hexane)

الإجراء التجريبي

A mixture of 8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecane (100 mg, 0.30 mmol), 4-isopropoxy-3-methyl-benzoic acid (61 mg, 0.31 mmol) and HATU (119 mg, 0.31 mmol) was stirred in DCM (450 μL) and DMF (450 μL) for 5 minutes. Triethylamine (83 μL, 0.59 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with sat. aq. NaHCO3 (5 mL) and extracted with DCM (3×5 mL), dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel column chromatography (0-100% EtOAc/hexane) to give [8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone as a colorless oil (120 mg, 79%). ESI-MS m/z calc. 512.3. Found 513.3 (M+1)+; Retention time: 1.86 minutes (3 min run).

المصدر