HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174262Generated: October 30, 2026
Hydrochloric Acid → tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate
https://huagongshe.com/reaction/1174262
Participants
| Role | Name | HCID | Charge |
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| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | ethyl (5S)-3-(4-bromobenzyl)-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-2-oxotetrahydro-3-furancarboxylate | HCID 67406735 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | tert-butyl (1S)-1-[(2S)-4-(4-bromobenzyl)-5-oxotetrahydro-2-furanyl]-2-phenylethylcarbamate | HCID 86598818 | 94.6% |
Reaction Steps
A solution of the product from Example 92A (22.4 g) in ethanol (120 mL) was treated with LiOH monohydrate (8.0 g, 190.7 mmol) solution in water (30 mL) and the mixture was stirred at 25° C. for 16 hours. The mixture was cooled to 0° C., adjusted to pH 5 by addition of 4N HCl and partitioned between dichloromethane and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the concentrate in toluene (400 mL) was then heated at reflux for 18 hours, cooled and concentrated to give the title compound (18.4 g), which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07834043B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-bca720b1212c459aba21c7687ab1d6f9 |
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| Source note | uspto-grants-2010_11 |
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