반응 #68813

반응 방정식

13a

5-[4-(Carboxymethoxy)phenyl]-15-[1,5-bis(dimethoxyphosphoryloxy)pent-3-yl]porphyrin

TMS-Br

→

solid

수율 76.0%

5-(4-(Carboxymethoxy)phenyl)-15-[1,5-bis(dihydroxyphosphoryloxy)pent-3-yl]porphyrin

수율 76.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타The solvents were evaporated at reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in MeOH (3.0 mL)
3. 3
   workup.STIRRINGThe solution was stirred for 1 h at room temperature
4. 4
   기타The volatile components were evaporated
5. 5
   workup.DISSOLUTIONThe solid residue was dissolved in ˜0.2 mL aqueous NaOH (15 wt %)
6. 6
   workup.ADDITIONthe sample was diluted to ˜3 mL with water
7. 7
   기타The sample was chromatographed (silica C-18, water/MeOH, 0→50%)

실험 절차

A sample of thoroughly dried 13a (11.8 mg, 0.015 mmol) was dissolved in dry CH2Cl2 (2.0 mL) and then treated with TMS-Br (100 μL, 0.760 mmol). The reaction mixture was stirred at room temperature for 3 h under argon. The solvents were evaporated at reduced pressure. The residue was dissolved in MeOH (3.0 mL). The solution was stirred for 1 h at room temperature. The volatile components were evaporated. The solid residue was dissolved in ˜0.2 mL aqueous NaOH (15 wt %), and the sample was diluted to ˜3 mL with water. The sample was chromatographed (silica C-18, water/MeOH, 0→50%) to afford a dark red solid (8.2 mg, 76%): 1H NMR 6 (D2O) 3.61 (m, 4H), 3.95 (m, 2H), 4.33 (m, 2H), 5.04 (s, 2H), 5.89 (m, 1H), 7.57 (d, J=7.8 Hz, 2H), 7.94-7.97 (m, 2H), 8.91 (m, 2H), 9.28-9.34 (m, 2H), 9.78-9.82 (m, 2H), 10.24-10.33 (m, 4H); ESI-MS obsd (+) 362.1 (M+2H)2+, 723.1 (M+H)+, 745.1 (M+Na)+ (−) 721.1 (M−H)−, calcd 722.15 (M, M=C33H32N4O11P2); λabs 402, 506 nm; λem (λexc 402 nm) 628, 688 nm; HPLC (20% B, 1.5 mL/min, tR=2.22 min).

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