Methanol → (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester

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Reaction Steps

A solution of 0.72 g (1.05 mmol) (2S,4R)-6-(2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl)-1H-benzo[d][1,3]oxazine-2,4-dione in 40 ml CH2Cl2 was treated at room temperature with 0.42 ml (10.5 mmol) MeOH and 0.31 ml (2.09 mmol) DBU and stirred for 6 h. Flash chromatography on silica gel (Hexane/EtOAc 9:1) gave (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester which was deprotected (following Method 3) to give (2S,4R)-2-amino-5-[2-benzyloxymethyl-4-mercapto-pyrrolidine-1-sulfonyl]-benzoic acid methyl ester, MS: 437 (M+H+).

Provenance & Evidence