반응 #160192

반응 방정식

Triethylamine

4-benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane

4-isopropoxy-3-methyl-benzoic acid

HATU

→

(10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

수율 100.0%

용매

DCM

DMF

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   workup.ADDITIONdiluted with sat. aq. NaHCO3
3. 3
   추출extracted with ethyl acetate (3×2 mL)
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타purified by silica gel column chromatography

실험 절차

A mixture of 4-benzyl-2-phenyl-1-oxa-4,9-diazaspiro[5.5]undecane (222 mg, 0.69 mmol), 4-isopropoxy-3-methyl-benzoic acid (140 mg, 0.72 mmol) and HATU (262 mg, 0.69 mmol) was stirred in a mixture of DCM (1 mL) and DMF (1 mL) for 5 minutes. Triethylamine (192 μL, 1.38 mmol) was added and the reaction mixture was stirred for 16 hours, then concentrated in vacuo, diluted with sat. aq. NaHCO3, extracted with ethyl acetate (3×2 mL), dried over MgSO4, filtered and concentrated in vacuo and purified by silica gel column chromatography using 0-60% EtOAc/DCM as eluent to give (10-benzyl-8-phenyl-7-oxa-3,10-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (343 mg, 100%) as a yellow oil. ESI-MS m/z calc. 406.5. Found 407.7 (M+1)+; Retention time: 1.13 minutes (3 min run).

출처