Reaction #171000

Reaction equation

6-[4-(2-Benzyloxyacetylamino)-phenoxy]-hexanoic acid methyl ester

6-[4-(2-Benzyloxy-acetylamino)-phenoxy]-hexanoic acid methyl ester

→

54

Yield 65.3%

6-[4-(2-Hydroxyacetylamino)-phenoxy]-hexanoic acid methyl ester

Yield 65.3%

Solvents

methanol

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration and methanol
2. 2
   workup.DISTILLATIONdistilled off
3. 3
   OtherCrude 54 was recrystallised in chloroform:hexane (1:6)

Procedure

6-[4-(2-Benzyloxyacetylamino)-phenoxy]-hexanoic acid methyl ester 53 (1 grams, 2.6 mmol) was dissolved in methanol (10 ml) in a pressure vessel. Palladium on carbon (5%, 250 mg) was added and the mixture stirred under a hydrogen atmosphere (2 kg) for 5 hrs. Catalyst was removed by filtration and methanol distilled off. Crude 54 was recrystallised in chloroform:hexane (1:6) to get pure 54 (0.5 g, 65.3%) as a white powder with an m.p. between 91.5-94° C. IH NMR (CDCl3) δ 1.45 (m, 2H, CH2), 1.62 (m, 4H, CH2x2), 2.36 (t, 2H, CH2), 3.02 (t, 2H, CH2), 3.02 (t, 1H, OH), 3.68 (s, 3H, Ester), 3.92 (t, 2H, CH2), 4.22 (d, 2H, CH2), 6.84 (d, 2H, Ar), 7.46 (d, 2H, Ar), 8.24 (bs, 1H, NH).

Source