Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Boc-D-phenylalanine | HCID 637610 | — |
| Reactant | methyl L-prolinate hydrochloride | HCID 2733200 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11567002 | HCID 11567002 | — |
Reaction Steps
To a cold (0° C.) solution of Boc-D-Phe-OH (5 g) in N,N-dimethyl formamide (200 ml) were successively added 1-hydroxy benzotriazole (4.29 g), dicyclohexyl carbodimide (4.29 g), H-Pro-OMe.HCl (3.1 g) and N-ethylmorpholine (3 ml). The mixture was stirred at 0° C. for 1 hour and then kept at room temperature for 2 days. The mixture was cooled to −20° C. and dicyclohexylurea was removed by filtration. The filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and washed successively with 5% sodium hydrogen carbonate, 0.1M hydrogen chloride-solution, saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel in heptane/ethyl acetate=6/4 (v/v) as eluent. The fractions containing Boc-D-Phe-Pro-OMe were pooled and evaporated. Yield: 1.5 g.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06432921B1 |
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| Source dataset | uspto-grants-2002_08 |
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| ORD ID | ord-7a93517c993e4b8c88e8cc8e51755cbe |
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| Source note | uspto-grants-2002_08 |
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