Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | D-Tryptophan | HCID 9060 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) 2-(2,5-dioxo-1-pyrrolidinyl) ester, (2S)- | HCID 853883 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | BocPro-DTrpOH | HCID 131713757 | 86% |
Reaction Steps
A chilled mixture of BocProOSu (96.1 mmole.) and dimethylformamide (100 ml.) was added with cooling to 0° C. to a solution of HDTrpOH (0.1 mole) and potassium hydroxide (85%, 0.1 mole) in dimethylformamide (150 ml.) and water (25 ml.). The mixture was stirred for one hour at 0° C., allowed to warm to room temperature overnight, and stripped of volatiles. The residue was partitioned between ethyl acetate and aqueous citric acid (5%). Crystals which formed between the layers were collected by filtration and recrystallized from methanol-water. More product was obtained by stripping the ethyl acetate layer of ethyl acetate and recrystallizing the residue from methanol-water. The recrystallizates were combined, affording BocProD-TrpOH in 86% yield (33.1 g., m.r. 210°-213° C.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04472305 |
|---|
| Source dataset | uspto-grants-1984_09 |
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| ORD ID | ord-3fb8309c9c354afa82168c3488c219f9 |
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| Source note | uspto-grants-1984_09 |
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