Imidazole → 5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

Participants

Reaction Steps

Analogously to Example 1i), 0.93 g (2.10 mmol) of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxy-phenylmethyl)-hexanoic acid in 20 ml of DMF is silylated with 1.4 g (9.64 mmol) of tert-butyldimethylchlorosilane and 1.17 g (17.2 mmol) of imidazole. The silyl ester function is hydrolysed with 1.7 g of potassium carbonate in methanol (23 ml)/THF (7 ml)/water (7 ml) and the crude product is stirred in hexane to give the title compound; tRet (I)=20.6 min; FAB-MS (M+H)+ =558.

Provenance & Evidence