反応 #69702

反応方程式

2,4-bis-benzyloxy-5-isopropyl-benzoic acid

5-nitroisoindoline

trifluoroacetate

EDAC

HOBt

NEt3

→

(2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone

溶媒

DMF

反応条件

後処理

1. 1
   その他then evaporated in vacuo
2. 2
   その他The residue was partitioned between EtOAc and 2M HCl
3. 3
   その他the EtOAc layer was separated
4. 4
   洗浄washed with saturated NaHCO3
5. 5
   乾燥dried (MgSO4)
6. 6
   その他evaporated
7. 7
   その他Purification by flash column chromatography (1:4

実験手順

A solution of 2,4-bis-benzyloxy-5-isopropyl-benzoic acid (505 mg; 1.3 mmol) (Preparation B5), 5-nitroisoindoline, trifluoroacetate (360 mg; 1 equiv.), EDAC (300 mg; 1.2 equiv.), HOBt (210 mg; 1.2 equiv.) and NEt3 (270 μA; 1.5 equiv.) in DMF (10 ml) was stirred at room temperature overnight then evaporated in vacuo. The residue was partitioned between EtOAc and 2M HCl, the EtOAc layer was separated, washed with saturated NaHCO3, dried (MgSO4) and evaporated. Purification by flash column chromatography (1:4 then 1:2 then 1:1 EtOAc/P.E. as eluant) gave 460 mg of (2,4-bis-benzyloxy-5-isopropyl-phenyl)-(5-nitro-1,3-dihydro-isoindol-2-yl)methanone. MS: [M+H]+ 523.

出典