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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 987962Generated: October 30, 2026

2-Naphthylalanine → (1S,5S)-(1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid Methyl Ester

https://huagongshe.com/reaction/987962

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-NaphthylalanineHCID 185915—
Reactant1-Naphthyl-L-alanineHCID 2724883—
Reactant2-Methoxycarbonylamino-3-naphthalen-2-yl-propionic acidHCID 18009002—
Reactant(1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamideHCID 20595420—
Product(1S,5S)-(1-{5-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2-naphthalen-2-yl-ethyl)-carbamic Acid Methyl EsterHCID 513951—

Reaction Steps

The title compound was prepared from (1S)-4-amino-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-benzenesulfonamide (XII) (example 28, step D) as described in general procedure B using L-2-naphthylalanine. The L-2-naphthylalanine was initially transformed into its 2-methoxycarbonylamino-3-naphthalen-2-yl-propionic acid derivative following the procedure used for L-1-naphthylalanine (example 28, step E). The final product was obtained in 41% yield (165 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06632816B1
Source datasetuspto-grants-2003_10
ORD IDord-f38393835beb47b6821c390ed09840a3
Source noteuspto-grants-2003_10