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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 929901Generated: October 30, 2026

Sodium Hydroxide → HCID 58319586, compound

https://huagongshe.com/reaction/929901

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium HydroxideHCID 14798—
ReactantBicyclo[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—
SolventEthanolHCID 702—
SolventTetrahydrofuranHCID 8028—
ProductHCID 58319586HCID 5831958696.3%

Reaction Conditions

Temperature60 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09296710B2
Source datasetuspto-grants-2016_03
ORD IDord-62ce0ae992584cec8138ac32b69eeaea
Source noteuspto-grants-2016_03