Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 1-Naphthalenepropanal | HCID 11041409 | — |
| Reactant | L-leucyl-L-tryptophan benzyl ester | HCID 15199902 | — |
| Reactant | Dibenzylphosphite | HCID 21904359 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178445940 | HCID 178445940 | — |
Reaction Steps
A mixture of L-leucyl-L-tryptophan benzyl ester (408 mg) and 3-(1-naphthyl)propionaldehyde (220 mg) in toluene (10 ml) was heated to reflux in a Dean-Stark apparatus for 2 hours. After cooling, dibenzyl phosphite (252 mg) and acetonitrile (10 ml) were added to the mixture and the resulting solution was stirred at 100° C. for 16 hours. After being cooled to room temperature, the mixture was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography (chloroform:ethyl acetate=5:1) to give two diastereomers of the title compound as colorless oil (a: 58 mg, b: 95 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05380921 |
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| Source dataset | uspto-grants-1995_01 |
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| ORD ID | ord-a2fe93a780e84d09851c811468f21b05 |
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| Source note | uspto-grants-1995_01 |
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