반응 #2275154

반응 방정식

(2R)-(t-butyloxycarbonylamino)-5-iodopentanoic acid t-butyl ester

Sodium hydride

phthalimide

→

(2R)-(t-butyloxycarbonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid t-butyl ester

수율 100.0%

용매

DMF

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGthe solution is stirred at RT for 30 min
2. 2
   workup.WAITat 60° C. for 8 h
3. 3
   기타The solvent is removed under reduced pressure
4. 4
   기타the residue is partitioned between 300 mL of ethyl acetate and 225 mL of 0.05M aqueous HCl
5. 5
   세척The organic phase is washed with 100 mL water and 50 mL of brine
6. 6
   건조dried over anhydrous Na2SO4
7. 7
   농축concentrated

실험 절차

Sodium hydride (0.522 g,13.05 mmol) is added to a solution of phthalimide (2.33 g, 15.84 mmol) and 18-crown-6 (0.01 g) in 20 mL of N,N-dimethylformamide (DMF). After stirring at RT for 20 min, a solution of the title F compound, (2R)-(t-butyloxycarbonylamino)-5-iodopentanoic acid t-butyl ester (4.61 g,11.55 mmol) in 5 mL of DMF is added, and the solution is stirred at RT for 30 min, then at 60° C. for 8 h. The solvent is removed under reduced pressure, and the residue is partitioned between 300 mL of ethyl acetate and 225 mL of 0.05M aqueous HCl. The organic phase is washed with 100 mL water and 50 mL of brine, dried over anhydrous Na2SO4 and concentrated to give 4.83 g (100%) of (2R)-(t-butyloxycarbonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid t-butyl ester as a tan solid: NMR(CDCl3) 1.43 (s, 9H), 1.45 (s, 9H), 1.60-1.88 (m, 4H), 3.71 (t, 2H, J=6.6), 4.18-4.26 (m, 1H), 5.06 (br d, 1H, J=7.9), 7.70-7.73 (m, 2H), 7.83-7.86 (m, 2H); IR 1712, 1500, 1155; ESI-MS 290 (M++1).

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