HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2122037Generated: November 2, 2026
Citric Acid → (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane
https://huagongshe.com/reaction/2122037
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | 1,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate | HCID 7146645 | — |
| Solvent | Water | HCID 962 | — |
| Product | (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane | HCID 9903372 | 95% |
Reaction Steps
(2S,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (3.57 g) was added to a mixed solution (35.7 ml) of ethanol and water (97:3), and they were stirred at 27° C. for 22 hours and then at 33° C. for 4 hours. 11.3% aqueous citric acid solution (40.3 g) was added to the obtained mixture, and they were cooled to −10° C. The crystals thus formed were taken by the filtration, washed with water (35.7 ml) and dried under reduced pressure to obtain intended (2S,3S)-3-tert-butoxycarbonylamino-1,2-epoxy-4-phenylbutane (2.88 g) in a yield of 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06696571B2 |
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| Source dataset | uspto-grants-2004_02 |
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| ORD ID | ord-0f16145046c4437e90dc7df5f0cbde19 |
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| Source note | uspto-grants-2004_02 |
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