HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 929901Generated: October 30, 2026
Sodium Hydroxide → HCID 58319586, compound
https://huagongshe.com/reaction/929901
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-oxo-, 2,6-bis(1,1-dimethylethyl) ester, (1S,2S,5R,6R)- | HCID 59712878 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58319586 | HCID 58319586 | 96.3% |
Reaction Steps
Add 2.5M sodium hydroxide (15.55 mL, 38.88 mmol) to a stirred solution of the ditert-butyl(1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.0 g, 4.86 mmol) in tetrahydrofuran (24.3 mL) and ethanol (9.72 mL). Heat the reaction mixture to 60° C. and maintain stirring overnight. Continue heating for 4 hours then wash with ethyl acetate. Cool the aqueous phase in an ice bath and acidify to pH=2-3 with 1N hydrochloric acid solution. Extract with ethyl acetate (3 times), dry the organic on sodium sulfate, filter and concentrate to give the title compound as an orange solid (1.4 g, 96%). MS (m/z): 322 (M+23).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09296710B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-62ce0ae992584cec8138ac32b69eeaea |
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| Source note | uspto-grants-2016_03 |
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